


BSU - Part 1

by TalesFromWherever



Series: Butt Slut University [1]
Category: Original Work
Genre: Alcohol, Anal Fingering, Blackmail, College, Confusion, Crossdressing, Crossdressing Kink, Embarrassment, F/M, Feminization, Forced Crossdressing, Forced Feminization, Lingerie, Male-Female Friendship, Masturbation, Mildly Dubious Consent, Muscles, POV Alternating, POV Female Character, POV Male Character, POV Multiple, POV Third Person, Prostate Massage, Sex, Sexual Confusion, Shame, Shaving, Vaginal Sex, non
Language: English
Status: Completed
Published: 2020-09-09
Updated: 2020-09-09
Packaged: 2021-03-07 01:21:37
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 17
Words: 25,233
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26378728
Author URL: https://archiveofourown.org/users/TalesFromWherever/pseuds/TalesFromWherever
Summary: Jack is a first year student at Barrington State University (Non-Covid universe).  After going out with his girlfriend to a fraternity party one night, he got angry as she ignored him and talked to a frat brother. Drinking more than he could handle, he stumbled home to watch some porn and take care of himself.  Accidentally turning on a trans video, he jerked off to it anyway before passing out. When he woke up, he found that his girlfriend had walked in to find him, with feminization videos on his computer. Feeling bad that she had left him at the party, and thinking that feminization was what Jack wanted, Chrissy did what any good girlfriend would do and decided to help her boyfriend be who he wanted to be!The only problem is, that isn't who Jack wants to be! But too scared to speak up, he goes along with it. As he got deeper and deeper into it, he realized he was enjoying it!
Relationships: Jack & Chrissy, Jack & Jayne
Series: Butt Slut University [1]
Series URL: https://archiveofourown.org/series/1917058
Kudos: 15





	1. Chapter 1

**Author's Note:**

> This is my first time writing a story at all. I come from an RP background and only after re-reading it did I realize that I wrote it as an RP. Each character gets a paragraph, alternating back and forth except for times that the protagonist is alone or doing something major. I've edited for grammar, spelling and punctuation, as well as polished over it a little. I am slowly trying to remove as many of the "began"s and other overly repeated words that I don't realize I'm using, so if you have any feedback, tips or suggestions I am all ears!
> 
> I also have plenty of plans for Part 2 and more. I just wanted to get feedback on the story so far to know that I'm on a good track, no point in writing a novel if people won't read past the first few chapters. As for the chapters, I was a bit lax with handing them out in the beginning and ended up with 50 chapters, each about a page. There's really only about 15-20 scenes of varying length, and I need to fix that.
> 
> Note that I added the non-con tag because of the Jayne scene. Its a shade of dubious consent as there isn't any blackmail levied, but I figure I should add it just in case. Don't want to ruin anyone's day.
> 
> Also, I have gone light on the kinks and sex to start. Things will progress, things may get crazy, things may go in all different directions. Still figuring all of that out.
> 
> Update 1: Edited down the chapters from 49 to 17. Might have one or two more than needed but I think their length is a bit better now. The work continues.  
> Update 2: Figured out AO3's chapter stuff, tomorrow when I have time I'll give them names and tag themes.  
> Update 3: Woke up to my first couple of Kudos, thank you for reading!

Barrington State University - BSU - Butt Slut University 

Chapter 1 

Jack stood in front of the mirror in his small single dorm room, stuffing his hands in the pockets of his jeans while angling his head, trying to look cool. He pulled one hand out and pointed his finger like a gun, suddenly feeling like a loser. He shook his hand out, choosing to focus on his clothes instead. He thought he had decent style, wearing a vest over a button down. Jack thought that college would be better than high school, but it ended up being more of the same. He had been cursed with averageness. He was not tall, he was not built, he was not super smart; there was extraordinarily little about him that was anything more than ordinary. His black hair was a bit long for a guy, always trying for that messy look but instead looking like he tried too hard. He had a girlfriend, but she loved to go out to frat parties and the guys there were such jerks. He just wanted to fit in. He fiddled with his hair, pushing it forward and then slicking it back again. 

His phone lit up and his girlfriend's ringtone began to play, sending Jack running across the room to answer it. "Hey babe, you're here? Alright I'll meet you downstairs." He stuffed his phone in his pocket and turned off his TV before patting himself all over. "Wallet, Keys, Phone, alright good to go!" he said to himself before heading out. Stepping out into the hallway, he turned back to lock his door, then jiggled it to make sure it was locked. Some called him uptight, but he just liked to be safe with all his stuff. He ALWAYS made sure of things like that. 

"Hey Jack, meeting that girlfriend of yours?" Came a gruff but feminine voice from the dorm room next to his. He looked in the open door to see his neighbor, Jayne, doing pushups. Jayne was one of those girls who was convinced she could become a fitness influencer. When she was not at the gym or running around campus, she could be found doing Booty Boot Camp in her room. She did not care too much for campus life because as she figured it, she would be famous soon enough. Jayne got up and walked to the entrance to her room, putting her hands on the top of the frame. Sweat glistened on the parts of her skin that were not covered in tight Lycra. "I don't get how a scrawny dude like you could get her!" She teased, causing Jack to frown a little. "Oh, don't be such a sissy, I was just kidding! Have fun tonight" she said before heading back to do squats. 

"Thanks Jayne, hey, break a leg in there" he lamely retorted, watching for a few seconds as Jayne's ass bobbed up and down. She could probably crush him with her thighs, so he walked off down the hall feeling like his night was already off to a bad start. 

After a short elevator trip down, Jack walked out of the dormitory building and into the cool night air. Outside in the parking lot attached to the dorm building, a blonde leaned against her car. She was wearing a pair of jeans that hugged her curves along with a black tube top that hid her B cup breasts, except for a bit of cleavage in the center. She got up as Jack stepped outside, and he smiled at her, the one good thing in his life. "Hey Chrissy, you ready to go? I thought we could hit up Luigi's Pizza, they're doing a game night tonight that I thought would be fun". He walked to her and gave her a kiss. At 5'7 to her 5'6, they were almost the same height. Even though they were both first-year students, Chrissy lived off campus. Her parents were well off and had gotten her an apartment and a car for getting into college. She never made money an issue, but Jack couldn't help feel lesser when she had to pay for him. 

"Ohhh...was that tonight?" she asked, pulling back from his kiss. "I reaaaaaally wanted to go to Alpha Chi for some beer pong tonight. I've just been so stressed with studying" she responded, looking at Jack with pouty eyes. He hated Alpha Chi the most, on more than one occasion they had allowed Chrissy in but not him. And he had really wanted to go to Luigi's! But he also wanted to keep his girlfriend happy. 

"Alpha Chi babe? But...those guys just suck!" he blurted out before quickly backpedaling. "But if it makes you happy, you've had an exhausting day. So, we can go." He forced a smile, but on the inside, he was groaning in defeat. 

"Awesome! Thanks Jack, I promise I won't let them stop you at the door this time, I'm cool with them now" She said, taking his hand and intertwining her fingers with his. As they turned and walked across campus to where the frats were, Chrissy's words rang in Jack's head. She was "cool" with them? Exactly what did that mean? How did she get "cool" with them when he was not around? Did she go to the frats without him that often? He couldn't shake the feeling that something was not right. 


	2. Chapter 2

Chapter 2

Frat row at Barrington State University was a noble and time-honored tradition. At least, that is what the brochure would have you believe. In reality, the row of large houses was more like an alcohol-soaked exercise in male dominance rituals. Several police cars remained parked on a corner, always ready in case something happened. Alpha Chi was the largest frat and was the first house on the corner of the row. The music from inside could be heard down the block. As they approached the building, they could see a line of people around the corner waiting to get in. "Oh, look at that, they're probably too full, might as well head back" Jack pressed his luck.

"No way, I told you I'm cool with them, watch this" Chrissy pulled him by his hand across the yard to the side of the house. There was a door on the side that was not lit, but Chrissy dragged them up to it. She knocked twice, then once, then twice again and the door opened a little, a stubbly face peering out.

"Yo’ what you want?" The Frat brother asked.

"I'm with Dijon" She replied, an apparent code that she had learned. The Frat brother opened the door allowing her in but went to close the door on Jack. "Hey, wait a minute I'm with her!" he whined at the taller guy. Chrissy reached back and grabbed his hand, pulling him inside "That's right, he's with me!" she exclaimed, dragging him off into the house. "Sorry about that, but hey I got you in!" Chrissy boasted happily, leading the two of them through people towards the house bar.

Bouncing off strangers as they got out of Chrissy's way but not Jack's, he apologized over and over. "Sorry, Pardon me, Excuse me, So...ahhhhh!" he yelped loudly as someone stepped into him, pouring some cold beer on his front, and leaving a wet spot on his jeans. Great, now it looked like he pissed himself. Could this night get any worse? They finally made their way to the bar and Chrissy got them red Solo cups of beer. At least the alcohol was free, he thought to himself, taking a big swig. He was here with his girlfriend, and that was all that really mattered.

"Hold on a second, I see my friend over there" Chrissy said, handing Jack her beer. Chrissy disappeared through the crowd to go hug a girl on the other side of the room, leaving Jack alone with his wet pants and sour mood. He drank some more of his beer, waiting impatiently as Chrissy talked to the other girl. Then, he watched as a tall frat brother walked up to the two of them and started to talk as well. Chrissy made no attempt to bring Jack over and seemed content to talk to the frat brother instead. Angry now, Jack pounded the rest of his beer and looked at the other one in his hand. He gulped it all down before tossing the cups on the floor and left.


	3. Chapter 3

Chapter 3

As he stumbled back across campus, Jack began to think it may not have been wise to pound both of those beers. He was slim for a guy at only 125 pounds, and that led to him being quite the lightweight. "Chrissy thinks that those frat guys are better than me, stupid frats" he mumbled to himself as he shambled across campus. After taking quite the long way back to his dorm, he fumbled around with his key card and finally managed to get in the building. A vertigo inducing elevator ride later and Jack had made it back to his room, taking several tries to get his key in the lock.

He plopped down in his desk chair, booting up his computer. Feeling pretty handsy and horny from his two beers, Jack pulled up his favorite porn site and began to search for things. He was having trouble typing and got no results for "Lebains". He tried typing it several more times but to no avail. Trying something else, he began to type "strap on" but only managed "trap".

The screen filled with thumbnails of hot chicks in skimpy outfits, and he loaded one up. Sitting back, he unzipped his jeans and tried to pull them off without getting up, ending up on the floor with his jeans around his knees. Finally kicking them off, he looked back at the screen to see the video had started. He stuffed his hand into his underwear and began to grope at his dick, another part of him that was cursed by averageness. The woman on screen was posing, rubbing her hands all over her body. Jack's cock hardened as he played, licking his lips drunkenly. "Mmm I bet she wouldn't leave me at a frat party, dumb Chrissy".

The woman began to strip, taking off her top to show off her flat chest. She began to play with her nipples and Jack jerked faster, getting more enthusiastic. "Where's the girl with the strap on?" he wondered aloud as he watched this Solo video. As the woman on screen pulled down her skirt, her underwear looked wrong. "Heh, she's all bulgy, what's wrong there?" Jack laughed to himself, his hand still stroking away.

And then she slipped out of her panties, revealing why there was a bulge. This woman had a dick. Jack had not been expecting that, but he did not stop watching. "I bet a girl with a dick would be cooler than Chrissy, probably play video games with me and not go to stupid frats." His hand had started to slap against his balls as he stroked, moving faster as she began to dance around naked and even stroke herself.

Feeling an orgasm coming on, Jack searched around for anything. He found a sock on the floor and quickly slipped it on over his cock just in time as he shot his load. His legs shook and he nearly fell over as a drunken orgasm rocked him, soaking the inside of the sock. Exhausted from the combination of alcohol and cumming, Jack fell forward onto his bed, passing out.


	4. Chapter 4

Chapter 4

Sunlight had flooded the room and he could feel a headache before his eyes even opened. He was in his room? How did he get back here? Was it...after the fight with Chrissy? He groaned and rolled over, wishing the sun would just go away. But another long day was just starting.

"Hello sleepyhead, did someone have a bit too much to drink last night?" Came Chrissy's familiar voice. Jack sat upright, his fight or flight response triggered by the sudden intrusion. "Hey, hey, calm down its just me, silly. Jayne was nice enough to let me in the building and your door was unlocked. Kinda lucky, you always lock it!" she beamed.

His door was unlocked? Visions of last night came flooding back to him. Fighting with Chrissy, stumbling home, jerking off and the porn stars di.... WAIT! He looked around the room in a hurry, first at his lap, then at his computer. He was wearing gym shorts like he usually slept in, but he did not remember changing last night. He turned towards his computer, seeing his normal home screen. Had he just dreamt that part? Yea, he must have. He would never jerk off to someone with a dick. Even if they were pretty hot...

"Oh, if you're worried about your little mess from last night, don't worry, I helped clean you up." She said, matter of factly. Chrissy stood up, wearing a pair of black leggings and a pink hoody, and walked over to the computer. She opened Jack's history and revealed a browser full of crossdressing porn. After Jack had passed out, the website continued to run through the next videos of a similar nature. At some point it had gotten onto a track about feminization, with videos like "My first time out dressed" and "Learning to use chastity".

"Last night I realized I had left you all alone but when I went to look for you, you had disappeared. I didn't hear from you the rest of the night, so I got worried and came here to apologize, but when I walked in... these videos were playing" she said, walking back over to Jack, sitting on the bed next to him. "We need to talk"

There was silence as Jack couldn't think of a single thing to say in his hung-over state. Time ticked on for what seemed like an eternity. Could he lie? Say that he did not know what she was talking about? Or say that they were just pop-ups. Yeah, that was it. They must have all just been pop ups after he left his computer on. But then Chrissy did something unexpected. She lunged forward and hugged him. "Oh baby, why didn't you tell me this is what you wanted? You know that I accept you, however you are" she exclaimed as she rubbed his back reassuringly.

Standing back up, Chrissy smiled "And while you were sleeping, I thought of something that could be a lot of fun for you. For both of us." She winked and took hold of her hoodie, pulling it off over her head. Underneath was a purple tank top, and she stripped out of that as well. Imitating a jazz bassline with her lips, she gave herself some music to strip to as she reached back to take off her bra. It slipped forward and she caught it, holding it against her chest with one hand and using her other to shake a finger at Jack. Finally pulling it off to reveal her breasts, she tossed the bra at Jack.

Turning away from him, she hooked her fingers into her tight leggings and bent over as she pulled them off. Down to just a white thong, she put a finger through the waistline and began to pull it off, only to pull it back up again. She ran her hand in a circle several times before finally stripping down completely, dropping her thong into the pile of clothes she had built up.

After last night's debacle and then his surprise wake-up, a strip tease from Chrissy was not how he thought he would start his morning. He was relieved that she had not just run screaming from the room after finding him like that, but he was a bit nervous about what she thought of it. He had not meant to jerk off to a trap, and he certainly did not know what that had to do with Chrissy's little tease, but he could already feel his blood rushing. He began to sit up, fighting against his raging headache.

But before he could get to what he thought was going to happen, Chrissy picked up the pile of clothes she had taken off and put it in his lap. "See, you can start with wearing that until you feel comfortable!" Chrissy walked over to Jack's dresser and pulled out a pair of boxers, sliding the masculine underwear up her legs and over her naked crotch. Then she grabbed one of his big t-shirts and hid her body away again, hopping into his computer chair to enjoy the show.

Looking down at the pile of clothes in his lap, Jack was confused. Why had she given him her clothes...to wear? He picked up Chrissy's thong, thinking through his hazy thoughts and remembered the woman in the video wore sexy clothes, did Chrissy really think... He put his hand to his head, wishing his hangover would go away. Finally getting a word in edgewise, Jack tried to get himself some time to think of a good story. "Hi baby, I just wanna say I'm sorry about last night. I didn't mean to run out on you like that" He tried contrition, hoping that he could talk her out of what she had in mind.

"Oh, don't you worry about that, it was my fault for not paying attention to you! If I had not been so caught up, I would have noticed all your cries for help. Always staying in your room, being scared of Alpha males, it all makes so much sense now. I must admit, I was worried when I first saw what you were watching. I thought maybe you were jerking off to that because you wanted to fuck them. But that would make you gay, and you are not, right?" she said, looking at him seriously.

Jack was caught in a corner. He could either admit he was jerking off to Trap porn, or he could wear girl's underwear. If he was truthful, she would surely break up with him. And tell everyone at school. And then his life would be over. Choosing the path of least resistance, he responded "No...no no! Definitely not. I love you and you know that! I'm sorry, I'm just a little nervous right now. I did not know if...I could trust you. With my secret." He looked down, his eyes resting on her clothes and turning away. He was really going to have to do this.

He went to stand up and felt dizzier than usual. "Do you think, do you think I could take a shower first? I really need one" He asked, hoping for more time but needed one regardless. He had not showered last night after all of that drinking and he felt hot and sticky. He did not want to get into Chrissy's clothes and have to give them back to her all dirty.

"That's a clever idea drunky, I'll join you. There's some things we could do in there as well." She gathered up Jack's shower supplies and a towel for each of them before helping him up. With one hand on him and the other carrying the pail of toiletries, she helped him out into the hallway.


	5. Chapter 5

Chapter 5

Some of Jack's dormmates were awake already and playing games in the communal area. "Whoa, Jack, looks like you had a rough night" said Billy, a taller guy who lived on the other side of the floor.

"Hey, leave him alone, he's a lightweight" teased Jayne, slamming down a draw 4 card as she whipped Billy at Uno. Jack blushed at their taunts, even more so as Chrissy helped him to the bathroom. He felt a bit helpless, partially from just being hungover, but it also seemed like everyone else had their lives figured out while he was still floundering.

Chrissy got Jack into one of the shower stalls, pulling his top and underwear from her body before giving him a hand with his. She tossed all the clothes over the side of the shower stall before turning on the hot water and pushing Jack underneath it. She rubbed his back with the water, just to warm him up and get him feeling human again. "There isn't that better baby?" she asked, wrapping her arms around his body from behind and pressing hers to his.

The feeling of the hot water began to wake Jack up and bring him from his stupor, almost as much as the feeling of Chrissy's chest pressed against him. He would have preferred to have been the one facing her, to give his cock something to rub up against, but this was nice as well. But as soon as he was getting used to it, she let go of him and reached outside of the stall.

Picking up Jack's bar of soap from his pail, Chrissy ran it over his back before turning him around and washing his front. Her hand slipped down to his crotch, making sure to get it nice and soapy. As they stood face to face, Chrissy smiled and pecked him on the lips. She could feel his cock hardening in her hands, happy to know that it still got hard for her. But for right now, she did not need it to be.

"Mmm that feels really good, please don't stop" he moaned, closing his eyes as she soaped him up. But his hopes for a nice early morning shower handy to start the day were quickly dashed as she pulled her hand away. Jack wanted to argue, but with everything going on he felt like anything could send his girlfriend down a bad path that he would not be able to come back from. If he just played along for a little bit, maybe she would get bored.

Chrissy reached outside of the shower again, this time for Jack's razor and shaving cream. Taking the cream in one hand, she spurted it into the other, surprised by how fast it came out. "Oh my! I didn't think it would be that fast" She said, not thinking of how that may sound if there was someone else in the bathroom. She put the can down and rubbed the cream in her hands, reaching out for Jack's dick again. She covered it in the white substance before continuing down to his balls. "There's just so much shaving cream here, I don't want to waste any of your stuff" she said, slipping her finger under his legs and covering his taint as well.

Jack wondered what she was going to do with the shaving cream until she started to practically jerk him off with it. Realizing that he was about to lose all the pubes he had waited so long for to grow in, Jack frowned. And as Chrissy's hand moved to a space he had never been touched before; his eyes went wide. Things were so out of hand, how was he ever going to get back?

Getting to her knees, Chrissy took the razor in hand. "Don't worry, I'll be careful with it" she giggled, pressing the razor to his skin below his belly button and lowered it, starting the first of his feminization ordeals. The hairs from Jack's waistline disappeared and soon she was working on the tuft above his cock. She hummed quietly as she worked, carefully pressing the razor to his body as she sheared off his body hair. It was not long until she turned him towards the falling water, cleaning the remaining shaving cream from his dick and revealing baby smooth skin.

Jack looked down at his package and felt like he was 12 again, his cock sticking out soft and hairless. Usually when Chrissy was on her knees in front of him, he was hard as a rock! But at some point, during this shaving session he had gone soft and now it would not go back up! He bit his lip, trying to will himself to get hard. Maybe now that he was shaved, his cock would look that much bigger and she would forget all about this. But her hand on his thigh began to twist him around, facing him away from her.

"Now reach back and spread your butt cheeks!" she giggled, causing a first-year student who had just walked into the bathroom to walk right back out. Still on her knees, she looked up at Jack's confused face. "What's wrong baby, is...this not what you wanted?" She asked, her lips pouting up slightly as she wondered if she was doing something wrong.

Looking down at his gorgeous girlfriend, he felt defeated. He never wanted to say no to her but right now he felt like he couldn't. "Nothing's wrong, I'm just...hungover" he mumbled, turning away in shame. He hung his head under the water, feeling it wash over him and alleviate his headache a little bit. He couldn't deal with this, not right now. It would just be easier to get it over with. He spread his legs a little and planted his feet, leaning over until his head rested against the cold shower tile. Reaching behind himself, he took hold of the soft skin back there and spread himself. "Like this babe?" He asked, trying to be good.

She had never seen a guy's asshole up close like this and she couldn't help but giggle. "That's perfect babe, is this what I look like, like that?" she asked with a smile on her face. Reaching between his legs, she took hold of his still shaving cream covered ball sac. Being super careful with the precarious skin, she worked her way from Jack's balls back to his butt. Getting back up for a second, she grabbed the shaving cream can. Pointing it at his browneye, she pressed the button and sent a load of shaving cream firmly against his hole. The surprise shot of cream hit his butt, giving him a sensation he had never felt before.

"See it is pretty sensitive to the touch Mister!" She giggled. Jack had been guilty of rubbing her hole with his finger during sex, hoping to coax her into trying something new. Now it seems the tables were turned. She rubbed the slick gel all over, getting his cheeks, underneath and even directly on his tight rosebud. "Relax! I'm not gonna do anything, I promise!"

The feeling of the expanding gel back there was so weird to Jack. Well, weirder than being lodged against the wall spreading his butt cheeks in front of his girlfriend. As her finger grazed against his hole, a tingling sensation in his crotch gave Jack cause for worry. His cock began to bobble, rising a little bit as the blood began to flow. Was he getting hard from her touching him back there? No way, it was just a delayed reaction to seeing her naked, he thought, trying to convince himself.

Chrissy brought the razor to his butt and began to work. She had a gentle touch, the sharp tool just grazing his peach skin. Working slowly, Chrissy deftly removed the boy's butt hair, leaving him with a baby smooth bottom. She twisted him so the water hit his back and cascaded down, a small river flowing directly between his cheeks and over his hole, clearing away all the excess cream. Leaning forward, she gave the soft skin on his left butt cheek a kiss before sliding back up to him. "There, all done sweety!" she said, putting the razor away. "How does it feel?"

The feeling of the water running on his ass was actually kind of...good. It spurred him on even more, giving him a little bit of a chub. He reached back to feel how smooth the skin on his butt was; his hands not daring to venture closer. "Oh, it feels...really nice, nice and smooth" he said meekly, unsure of what to say. Then he felt his hand shifted, slipped between his cheeks as Chrissy maneuvered his hand.

"It's not just the cheeks silly, feel how smooth this is?" She asked, guiding his fingers to graze against his butthole. It was quite the surprise, but she was right about it being silky. "Now there won't be any stray hairs when you dress! Turn around so I can see the front" she giggled, spinning her finger in the air at him. Jack balled up his fist, squeezing tightly as he told himself that everything would be OK. Turning to show her his hairless cock, he had to slap his hands to his ears as Chrissy let loose a high-pitched giggle.

"Ooooh! It’s so cute! And look, it even started to get hard!" Chrissy squealed, clapping her hands happily. She reached out and tapped his cock on the side, letting it swing back and forth a little bit. "I just can't wait to see it in my panties, I'll hurry up and get cleaned." She leaned her head back under the shower and let it wash over her completely, soaking her hair and her front.

Left to stand in the cold while Chrissy finished her shower, Jack nervously crossed his arms over his chest as he watched her. On a normal day, there was nothing he liked more than watching her shower. But now as she soaped up, his mind was racing too fast to enjoy it. He wished for time to stand still, for things to stop or slow down. But the cleaner Chrissy's body got, the sooner the future was to arrive.


	6. Chapter 6

Chapter 6

After wrapping themselves up in their towels, Chrissy's around her torso and Jack’s around his waist, the couple left the bathroom and headed back to Jack's room. Feeling better and able to move under his own power now, Jack carried the pail and their clothes as Chrissy held up her towel to make sure it would not fall from her small chest. Each step towards his room felt like a step towards a prison cell and he realized that there was no getting out of this. He was going to have to wear her clothes.

They stepped back into Jack's room and this time he made sure to lock the door, checking it a second time before turning away. Jack looked on as Chrissy went back to his dresser, rooting through it for a pair of gym shorts and a tee shirt. Standing there in just a towel, he watched as she looked in the mirror and rolled the waist of his shorts up until they were tighter on her ass, twisting her butt back and forth to make sure it fit correctly. He wanted to say something, to get the two of them back to normal, but Chrissy caught his gaze.

"What's wrong silly, it's your turn! Don't be nervous, it's just you and me in here" she looked softly on him, flashing a reassuring smile. She hopped onto his bed and lay on her stomach, kicking her legs up behind her as she ran the towel over her hair to dry it. "Alright, I'm all ready for the show."

Jack stepped over to the pile of her clothes, nervously reaching down to pick up her panties. He held the small white thong in his hand, stretching the waistband a little nervously. He had held Chrissy's panties plenty of times before, but this was quite different. As his fingers ran over the soft material, he thought about how everything had changed so quickly. It was now or never. Reaching down to let his towel fall to the floor, he quickly lowered the women's underwear in front of him and stepped into it.

Slipping it up his now shaved skin, Jack finally understood why women's underwear was made from the material it was. The soft fabric felt wonderful against his smooth skin. As he pulled it all the way up and it reached his sensitive package, he shivered. Was he enjoying this? No way, it was just nerves, everything felt different when he was nervous, he told himself, still clinging to hope that things would go back.

As Jack pulled the thong over his crotch, Chrissy watched intently. The fabric wrapped tightly around his cock and created an adorable bulge. "That...looks...SO CUTE!" she squealed, causing Jack to bring his finger to his mouth to shush her. "Ooops sorry!" she giggled, clasping her hand to her mouth. Chrissy had never thought about dating a crossdresser before, but as Jack began to dress, she wondered how she had waited this long!

The nervous boy felt a combination of shame and pride. Chrissy was a loving girlfriend, but she was complimenting him so much right now! He was glad for it, because he did not think that he would be able to get through this without. But if she had not been so encouraging, he would not be doing this at all, a small voice at the back of his head reminded him. But with his cock snug in a thong, it was too late for him to do anything. He had passed the point of no return.

He reached down and picked up Chrissy's leggings, holding them in the air to inspect them. The material was light and stretchy, and pretty darn soft. He thought about all his clothes and how scratchy they were, why didn't they make guy’s clothes like this? Shaking his head as he tried to get rid of the thought, he held the waistband of the leggings open and tried to step in. He was still a little hung over, so he bounced around trying to get his leg inside. Finally succeeding, the tight legging clung to him as it slid up his body, and he bounced a little to pull it up.

"Look at that butt jiggle!" Chrissy added from the peanut gallery. She couldn't believe that her boyfriend looked so good in girl's clothes! She began to make a mental checklist for the future as she watched him get dressed. There was so much fun stuff they could do like this, so much different stuff. This would not be like all her other boring relationships; this was new and exciting! She could feel her juices begin to flow, feeling like this was their first time again. In a way, it was.

When the soft material reached his freshly shaved skin, Jack's eyes widened a bit. He had been so used to clothes being uncomfortable that he had never thought that they could be...exceptionally comfortable. He pulled the curve-hugging pants past his butt and to his waist, feeling the crotch of the outfit pressing firmly on his underside. He was used to a little more room in that area, but these did not seem like the kind of pants one could sag.

"How did I never notice that your butt was so cute?" Chrissy asked from across the room. Her leggings had perked his butt up, giving him a good starting feminine frame. She hopped up from the bed and walked over to where Jack was standing, stepping behind him. She pulled on the leggings, making them even higher before rolling the top down once. They were a bit short on Jack, but they still looked adorable. "There, that's better, and let's see..." she wrapped her hands around his waist, her fingers sliding over his crotch. "...yep, let's just..." she fished a hand into the front of the leggings, finding Jack's cock. Before he could get too excited, she nimbly adjusted it so it was less of a pouch, pulling his dick upwards so it lay against his body.

His cock ached for more, but as Chrissy pulled her hand out and pat the front of the leggings, he realized it just was not in the cards. As he looked in the mirror, he was surprised by how good his lower half looked. He was not muscular, leaving his legs looking soft and feminine in the girly clothes. He felt Chrissy's hands leave his body as the girl went back to his bed, realizing he had to finish getting dressed.

Jack picked up the plain purple tank top, feeling thankful Chrissy had chosen such simple clothes to wear today. He was less hesitant about putting the top on, but Chrissy stopped him as he started. "Hey! You can't put a top on before your bra silly!" She coached from the bed. He looked down at the folded-up fabric on the floor, feeling kind of silly as he picked it up. The rest of the clothes were still clothes, but this...he did not have any tits. But as he looked over at Chrissy, she was happier than he had ever seen her. He held it up and slipped his arms through it, the bra falling forward as he tried to reach around behind him.

Chrissy hopped up again, really getting her workout in having to help Jack with all the clothes. She giggled and stepped up behind him again. "Here, let me baby" she said while swatting away his hands. Sometimes boys were just so cute when they fumbled with bras. "You're going to have to learn to do this on your own you know. It's going to take some practice, but you get used to it after a while!" She hooked the bra together and then reached around him to adjust. "See and you're going to want to put your boob in the cup, so it supports it." She picked up the tank top and the hoodie, handing him the top "You're almost there babe, I'm so proud of you."

Jack felt so confused. He was enjoying how supportive and loving Chrissy was being and it made him feel great. But at the same time, he had not been secretly hoping to dress as a girl! Taking the purple top from her, he slipped it on over his head. The dainty straps sat lightly on his shoulders, and the bottom came up just above the waistline of the leggings, showing off a bit of skin. He tried to pull it down a little to cover up his bulge, but the top was not long enough. He had to make do with the pink hoodie, pulling it on over his head. He felt better in thicker top, a bit more covered up. Looking in the mirror, he looked like a boy in girls' clothing, not knowing what else he expected. His face was still unmistakably masculine, but his body fit the girl's clothes well.

Chrissy let him look himself over for a second before grabbing him tightly. "Oh, it's perfect, my own little dress up doll!" she giggled, squeezing her arms around him happily. "Now, let's be lazy and watch a movie." Her arms let go of him and she strode over to the bed and lifted the covers. Sliding underneath it, she held the blanket up for Jack, patting the empty space next to her.

Jack looked at the bed, thinking about how he usually takes the far side. The TV was across from the bed so whoever was on the far side was inevitably the big spoon. Chrissy wanted him to be the little spoon. Was this how she thought of him now? He was still a bit hung over and all of this had tired him out, so without arguing it he got onto the bed with her.


	7. Chapter 7

Chapter 7

Underneath the covers, Chrissy pulled her body closer to Jack's, scooping one arm underneath him and wrapping the other over him from behind. Her clothes felt quite nice from this side of them, and she rubbed her face into the soft hoodie. Then, leaving one arm underneath Jack, she rolled over to grope around for his TV remote. Flipping it on, the Sci-Fi channel was on and there was a zombie movie playing. "Hey look, zombies your favorite babe! Wanna watch this?" she asked, wanting Jack to enjoy their day together.

Not used to being the small spoon, Jack did not know what to do with his hands. He tried to put them down by his side, but Chrissy had wrapped her arms around him. He settled on putting one hand on top of hers and the other under his head. He could feel her crotch pull tight to his butt, much more familiar with Chrissy's position than his own. This was usually the point he would begin to rub his dick against her to try to get her in the mood, but obviously that was not going to work like this. For a moment, he wondered what it felt like to Chrissy when he got hard, but quickly put it out of his mind. He did not want to find that out!

The movie was an old one, Zombies from Deep Space Four. He really liked it, but today he was having trouble focusing on the screen. His brain couldn't stop thinking about everything that was happening. Was this going to be how things were now? What if someone caught him? His brain would not stop racing as he began to overthink every situation moving forward. But then Chrissy's hand began to move from his waist.

"You just watch your movie babe, you let me take care of everything" she whispered in his ear from behind. Her move from his waist down to his ass, rubbing gently and tracing lines with her finger. "I gotta say, this all has gotten me so hot." She pressed two fingers against the side of his ass and began to walk them across his hips, each step bringing them closer to his cock. Finally, she twiddled her fingers over his bulge, gently resting her hand on top of it. She began to rub it up and down over the leggings, her fingers going much lower than they needed to.

Jack adjusted his body, pushing back against her a little bit to push his crotch up higher, giving her better access. At least this part felt the same, even if she was behind him. "Mmm that feels really nice" he moaned lightly, meaning the feeling of her hands on his crotch. The way she was rubbing him, well it felt like the way he rubbed her pussy, in soft circles right over her clit. Was she pretending he had a vag?

"I bet it does now that you're nice and shaved. Do those panties hug your little package all snugly?" She responded, meaning to be cute by calling it little. But from the way he winced, she could tell she struck a nerve. "Oh, I don't mean little babe, I just mean that it's so cute in my undies. Trust me, I really like it" she reassured him. "In fact, why don't you get up and I'll show you how much I like it." She pulled the covers off him and moved her arm, indicating for him to get up. Slipping off the bed, she got to her knees in front of the bed. Curling her fingers at him, she beckoned him off the bed.

That was more like it, Jack thought. A blowjob would get him feeling like himself again, and he would be able to get his cock out of these girly undies. He pulled himself to the edge of the bed and stood up, reaching his hands into the waistline of the leggings to take them off. But Chrissy's hands stopped him before he could.

"Hey, relax, let me do it babe" She said, reaching up his legs from her kneeling position in front of him. She ran her hands over the front of his thighs, up towards his crotch. Slipping them back down, she moved both hands to his left leg and pushed them up again. This time she moved one hand up his inner thigh, the feeling sending his balls tightening in reflex. He shuddered as his crotch felt a double pronged assault, one from the side and one from underneath. But just as he was getting used to this teasing, she began to twist his body to face away from her.

"Hey, what are you doing?" he asked, acquiescing to Chrissy's manhandling of him as he turned. He felt a little wobbly and put his hands out as he leaned over the bed, his ass now sticking out. Was this the way she wanted him? She was not going to try to fuck him or anything was she? That would be too much, he did not want that. He thought about putting an end to this, stopping it all right now and just breaking up with her. But how could he do that? She was the best woman he would ever be able to get, and now that she had done this to him, how could he ever get his dignity back? The worry for his butthole intensified as he felt her fingers pulling at the waistlines of both the thong and legging, his ass slowly being exposed as they were pulled down.

But before Jack could put an end to what was the best thing to happen to him, Chrissy reached up between his legs and took hold of his cock. It had started to harden, and she pulled it back between his legs, letting it rest on the thong that held his knees together. She began to stroke it, jerking him off in a way he had never experience before. Her hand stroked up and down, his cock pointing directly at the floor below them. She raised herself up to lick the tip of his cock, her tongue swirling around the head.

Jack had NEVER had a blowjob like this before, both the position and the way it made him feel. His legs instantly felt weak, and he had to adjust his stance to not fall over. The leggings and thong were only pulled down partially, keeping his legs stuck somewhat close. He couldn't widen his stance, so he just had to bend over farther. Moving his arms forward more on the bed, he pushed his butt backwards for better leverage, not realizing that he was girlishly sticking out his ass.

Chrissy was encouraged by Jack's shifting and licked a line up the underside of his cock to his balls. She began to kiss the smooth orbs as her hand stroked, angling his dick precariously with each movement. After giving his balls thorough attention, she began to kiss down the shaft and back to the head. Her mouth opened up to swallow the tip, blowing the boy from behind.

His cock had to bend backwards to accommodate the position that she had chosen, but he was not one to complain right now. Even from this awkward placement, it was one of the best hand/blowjobs he had ever received. Was it all from how he was standing? Or maybe...no, it was not the outfit, that had nothing to do with it. Maybe it was just Chrissy being extremely enthusiastic about this, he tried to convince himself. But her work was making it hard to concentrate and his fingers curled up into the bed sheets. He could already feel an orgasm welling up inside of him.

Taking hold of Jack's legs for support, Chrissy began to bob her head back and forth, sucking Jack's cock down deeper. She was not a slut or an expert, but with Jack's size it was not long until her nose was pressed against his balls from underneath, the entirety of his cock lodged in her throat. She held it there for a few seconds before pulling off to take a breath again, going back to stroking him. Her hand worked faster and faster, hammering him from below.

The way Chrissy was jerking had Jack's toes curling. He had been hoping to hold on long enough for sex, but as Chrissy's hand worked, he realized he was not going to make it. Blushing deeply, he knew he had to just let go. "I'm gonna...I'm gonna....Ahhhhh!" he whimpered out as he buried his face into the bedsheets. His cock jerked back, angling away from the clothes he was wearing as he began to spurt a load all over the floor.

Chrissy smiled as she nimbly worked Jack to orgasm, holding his cock tightly to make sure to milk out every last drop. She leaned back in again and gave his softening dick a kiss, sucking at the head lightly to get it nice and clean. Letting go, she took hold of Jack's thong and pulled it back up his body, nestling his sensitive member. Getting to her feet again, she pulled Jack's leggings back up, patting him on the butt to let him know he could rest. Grabbing a towel from his hamper, she washed up the cum puddle from the tile floor.

His mind was racing. There was just so much to process. That entire session was mind-blowing, from the way she sucked him to the way he came. But what about from here on out? Was he going to have to keep doing this? He figured it was better to leave those thoughts to another day. Right now, he was tired, and he just wanted to curl up with Chrissy and take a nap.

A phone ringing pierced the silence, and Chrissy went scrambling for her phone. "Oh hey, What's up? Wait what, its due when? Fuck. Alright, I'll head back home and then meet you soon." Chrissy put her phone down and looked at Jack, wanting to spend more time with him. "Babe that was just my friend from my Poli-Sci class, one of the people in our group just got kicked out of school and our teacher isn't going to give us an extension to do his part of it, so I have to run." She looked down at the clothes she was wearing, a pair of his gym shorts and a plain tee, that would be good enough. "You hold onto those and I'll just wear this home right now. Take a nap sweety, you look bushed."

Jack watched as his girlfriend gathered up her things, wishing that she could stay. He was so tired he was probably going to take her advice and take a nap. "Alright babe, I'm sorry that that happened. That teacher is a dick. Thank you for.... being so understanding" he added, not really knowing what to say about what had just happened.

His girlfriend crossed the room back to him and planted a big kiss on his lips, wrapping up his face with her hands. "It was wonderful; this really has been an enjoyable day!" She turned to leave the room, blowing him a kiss from the door and disappearing out into the hallway.

Jack lay back on his bed, looking at the TV to see that the movie was still playing. It was only noon and if you had told him about twelve hours ago that this was how his day would go, he would have thought you were crazy. He couldn't believe this had all happened just because he did not lock his door. He always locked his door! He should lock it now, he thought, putting a hand to his mouth and yawning. His eyes closed sleepily; the screams of an astronaut being eaten by a zombie lulling him to sleep.


	8. Chapter 8

Chapter 8

"Holy shit, you really are a sissy" Came the curt but feminine voice, rousing Jack again. Was everything that happened just a dream, who was talking to him now? His eyes opened to see Jayne standing over him, her hand over her mouth as she pointed at his body. He looked down to see he was laying on his bed, still wearing Chrissy's clothes. For a second everything felt normal, but then he remembered, HE WAS WEARING CHRISSY'S CLOTHES!

"What the fuck, how did you get in here?" he asked, looking around to figure out how he could best cover himself up. He couldn't take the clothes off now, he had girlier clothes on underneath. He grabbed the covers to his bed and pulled them over his body, holding them tight. "I'm not a sissy! I just....I..." he tried to think of something. He was no longer hung over, but the words just were not coming to him.

"You just need to learn to lock your door" she taunted, crossing her arms over her chest. She was wearing one of her workout outfits, a baby blue matching top and bottom. "I came over to borrow something and you weren't answering so I walked in because you haven't come out all day. I let Chrissy in her earlier and found you passed out with sissy porn on and she asked me not to tell anyone. I didn't think you were an actual sissy." She said, pulling the covers off his body to show off his outfit again. "It all makes sense now."

Jack felt his cheeks flushing as he found out that Jayne had seen it too, and now she was seeing this. He did not want to be a sissy and he had no intention of being a sissy, but now he had two women who thought he did! He thought that high school was the worst thing to happen to him, but little did he know that missing a single letter "S" while typing would change his life so much. Realizing that Jayne was not going to go away or let up, he sat up in bed, beginning to wake up. He shook his head at her, putting his hands into the pouch of the hoodie. "You said you wanted to borrow something, what did you want?"

Jayne stood over him puffing her chest out. "Trying to get rid of me that fast? Not gonna happen. I came over for the math homework that's due tomorrow but now that I see you like this; I think I want a little more." She moved closer and pulled off the hoodie he was wearing, unveiling the feminine tank top underneath. "And just how deep does this little sissy act of yours go?" she asked, bending down. She was a bit heavier chested than Chrissy, and her bust was dangerously close to his face. But she reached next to him and pulled on the side of his leggings, her finger grabbing a bit of thong underneath as well. "It goes all of the way. Well that settles it, show me.”

Jack grimaced, he had already had quite the day of dressing up for Chrissy, and now he was going to have to show Jayne as well? She was a lot pushier than Chrissy was and they were not dating, so Jayne didn’t have a reason to keep his secret. Gritting his teeth and making a mental note that he would ALWAYS check that he had locked his door from now on, he pushed her hand away. "Alright, alright already, stop, I'll show you, geez." He looked up at the fit girl, seeing her in a different way now that she was pushing him around.

Jack always felt like he had the upper hand in his relationship with Chrissy because he was a little bit taller and a bit bigger. But Jayne was 5'11 and stood well above him. She was not super muscular, but she could definitely lift more than he could. Dressed like a girl and being pushed around by this larger woman, it felt different. He stood up and reached his arm over his shoulder, pulling at the tank top from near the back of the neck until it came off over his head.

Jayne laughed "Still learning a lot are ya? Girls don't take their tops off like that dummy. They do it from the bottom, sexy-like you know?" She went and sat on his desk chair; her legs spread in a tomboyish manner. "Try it again, slower and better. You should be paying me for these lessons ya know? And for keeping your secret" she said with a wink.

"Well what about Chrissy? How's she gonna feel about you...looking at me like this?" he responded, not knowing how to define what exactly was happening right now. He thought about Chrissy and how much he missed her already. He was alone in his room with another girl, she would not be happy about something like this. It felt like cheating. But he also did not want to piss off his dorm neighbor, he had to walk an exceptionally fine line.

"I'll keep your secret, and you'll keep our secret" she said with a wink. She had no intention of stealing a little sissy like Jack away from Chrissy, but she did want to get some fun out of it. "Now come on, I don't have all day."

The nervous boy pulled the tank top back on over his head before trying to pull it off from the bottom. He had never done that before, so he picked at the fabric awkwardly as he tried to figure out how that worked. Getting a bit nervous, he stopped and took a breath before thinking to try crossing his arms. Finally, the fabric lifted off his body, coming up over his head. It was not that sexy, but it was a little bit of an improvement. He stood awkwardly in front of Jayne, having trouble decided which part of his body he wanted to cover up more, his bra covered flat chest or the front of his crotch.

"You're a long way from filling that in, you know sissy?" she laughed, looking at Jack's bra that hung off his body with nothing to hold onto. "You need a training bra for right now, something that's tight and hugs your body. Don't worry, I'll get you one from the gym." She added, she could always sneak into one of the lockers and find him something that would fit him. Jack may be a weird little sissy, but she had a soft spot for the boy. And with her busy training schedule, she did not have much time for dating. Having a little callboy next door could be helpful. "The leggings too sweety"

"Thanks?" he said, a bit confused as to what to do with that information. He agreed that a training bra would fit him better, and it was nice that she was willing to get him one, but it meant that he was going deeper and deeper down the rabbit hole. He went to hook his fingers into the waist of the leggings before stopping himself. He walked over to the door and made sure it was locked this time. Stepping back in front of Jayne, he went back to what he was doing and stripped the leggings from his body. He couldn't believe he was doing this, standing in front of her in just a bra and thong.

"Not bad for early in your transition. There are some things you can improve but I'll let Chrissy handle all of that. I've got a task for you instead." She stood up and walked over to him, putting her hands on his waist. Looking cleverly in his eyes, she shoved him back onto his bed. "Lay there like a good sissy" she commanded. There was authority in her voice as she said it and she stood over him off the bed. Reaching down and stripping out of her own tight leggings, she revealed a pussy that was shaved except for a little triangle patch above her clit. She smiled at Jack as she tossed the bottoms off to the side and knelt on the bed with next to him.

The dormitory bed creaked as the strong woman knelt on it, and Jack gulped loudly. He had never even thought of Jayne this way and he had no idea what was going to happen. Was he going to get to fuck her? His cock began to strain at his thong at the thought of it. He watched nervously, allowing Jayne to hold control. Allowed, he thought to himself, not much that I could do if I wanted to. "I don't want to cheat on Chrissy" he managed to squeak out nervously.

"Oh, don't worry, we won't do anything that will weigh too heavy on your conscience. You're going to be my little tongue slut today" She threw her powerful thigh over Jack's body, straddling his chest. With her body so close, the boy could catch her scent. She had just finished working out in her room and had come in to borrow some soap, needing for a shower. Instead, Jack was going to make a good replacement. She inched her crotch up his body, her pussy hovering over his face. "Stick your tongue out sissy."

The smell of her workout was heavy in his face as Jayne lowered down closer to Jack's mouth. With the way she was practically sitting on him, there was no escaping it. He thought of Chrissy, not wanting to do anything that would hurt her, but at the same time he was worried for himself in his current predicament. Going again with the path of least resistance, he shyly stuck out his tongue, barely poking it out of his mouth.

"If that's how you eat Chrissy out, I feel bad for her and I don't get how you keep her" she taunted, turning back and running a single finger over the bulge in his thong. "It's certainly not that thing." It was a bit of a low blow for her, some low hanging fruit, but she could tell that Jack needed the discipline. She would get some enjoyment, Jack would get some training, and Chrissy would benefit the same. "Now like I said, stick that tongue out and lick my pussy sissy" again issuing a command that was not to be trifled with.

Feeling like he was sinking into the bed, not under the weight of Jayne but of everything that was happening, he helplessly stuck his tongue out farther. From where his head was, he was just able to reach Jayne's crotch and his tongue touched her smooth mound, recoiling from the bitter taste. He couldn’t believe she worked up such a sweat in her room. But he was already stuck. What was a little ripeness on top of all the other humiliation he had suffered? He steeled himself and stuck his tongue out firmly, pressing it against Jayne's pussy lips and licking a line from top to bottom.

Reaching down to grab his hair, she ran her fingers through his black locks first to get a good grip. Lowering herself even more, she sat on the boy's face heavily, smothering his mouth with her crotch. She could feel his breath from his nostrils coming quickly as he couldn't breathe from his mouth and laughed, grinding her crotch into his face some more. "Relax sissy, you can breathe through your nose. All you need to do is be a good girl and lick it like your life depends on it." She slipped back and forth, rubbing her pussy around his mouth, soaking his chin and his cheek. "Get it nice and clean for me and I'll let you go"

Jack felt a rush of emotions that confused him even more. Fear, desire, betrayal, arousal; all of it swirled in his mind as he worked in a daze. The smell and taste of her was strong, but now that he was getting used to it, it was not so bad. The feeling of her hand on his head, guiding him, was scary but also reassuring. She was giving him all the help he could really ask for, working herself on his face. All he had to do was use his tongue well, that was not that bad. He used all the muscle he had in his mouth to push his tongue inside of her, penetrating her folds. He darted his tongue back and forth, rewarded by moaning from Jayne.

The invasion of the boys tongue inside of her was quite the welcome feeling, it was the first thing inside her other than her own fingers in quite a while. "That's it, see how many licks it takes to get to the center of the tootsie pop" she teased, holding on to the bed frame to better work herself on his face. She had not expected much from Jack, she was only glad he was clearing the bar. Reaching her hand down to play with her clit, she stopped moving back and forth and rubbed herself right in his face. "Stick your tongue nice and deep and swirl it around, come on, do it now!" she moaned at him.

Encouraged by her moaning, Jack reached up to hold onto her powerful thighs. Using his arms to help give him more leverage and push back against her grinding crotch, he dug his tongue inside of her, twisting it around as she had said. The shaking of her thighs around his face let him know he was doing it right, and he made sure to file that information away for next time Chrissy was over. That was definitely a bonus!

The girl's hand rubbing at her clit vigorously nearly kept smacking Jack in the face as Jayne got more aroused and primal. "Mmm fuck shove your tongue in right....theeeerreeeeee" she moaned, her eyes closing as her body tensed up. She raised up on her knees, her crotch no longer touching Jack's lips and began to shake. "Fuck, fuck, fuck, fuck, yesssss" the girl whined, her voice going higher than Jack had ever heard. Gripping Jack's face hard, she finally let go, squirting all over the boy and getting it all over his bed sheets.

The hot liquid was a surprise to Jack, he had seen videos of girls squirting before, but he had never made one squirt himself! He closed his eyes, feeling it blast him in the face as he was unable to protect himself, his arms trapped underneath Jayne's body. When the last squirt finally dribbled onto his chin, he opened his eyes to see if it was over. His bed sheets were soaked, as was his face and even his bra! "What....what was that?!" he asked in shock.

"A reward for a job well done sissy" Jayne replied, groaning as she finally got off the bed and stood back up again. She felt better than she had in days, that was just the thing she needed to loosen up for her workouts. She giggled girlishly as she looked at Jack still laying in place, his face shiny with her juices. His thong bulged out, no longer able to hide his hard on that had grown. Maybe the boy deserved a little something more. "Stand up and take that cock out" she commanded.


	9. Chapter 9

Chapter 9

Jack knew he had to obey Jayne, and he did not feel as bad about eating her out as he thought he would have. After all, he did not get any pleasure out of it, she used him! But now as he was made to stand and strip, he felt like he was dangerously toeing the line again. "But...Chrissy" he managed out, a look of sadness on his face.

"Don't worry about Chrissy, we're not fucking, dumbass. Come over here." She grabbed his arm and pulled him towards her, turning him away from her. "Alright, now no looking" she said, pulling off her workout top. Her C Cups spilled out, free from their sweaty prison. Standing behind him, she took hold of his waist and pressed her body to his, her nipples rubbing against his back. Leaning over, Jayne nibbled at Jack's ear from behind. "Now, because you were so good, I'm going to help you get off as well. Take out that cock"

Jack felt a bit more comfortable as Jayne pressed her body to his, feeling like this was not so bad. He nodded his head to let her know he would comply and reached down to pull the thong off his dick. His 5-inch cock sprang free and stood at attention, well rested from this morning's session. "It's out" he said with a shudder, feeling nervous, cold, and excited.

Jayne continued to rub herself against the boy's body, the stimulation against his soft skin feeling nice to her. "Good, now close your eyes and take it in your hand" she began to guide him with her voice, speaking much softer than her usual tone. "Picture Chrissy, wearing one of those sexy little outfits she wears. Even I think she's pretty darn hot." Her hands began to scratch lightly against the boy's waist, eliciting a moan from his lips.

He could picture her easily, Chrissy standing in front of him. He gave her his favorite outfit that she wore, a ripped and pleated plaid skirt along with a fishnet top and a band tee that she had worn to a concert with him. Jack had known then that he wanted to be with her. His cock got even harder has he thought about her, taking it in his hand as his large dominatrix had commanded. He couldn't help but begin to stroke, worried that Jayne would get mad.

It was just the opposite. "That's a good sissy, stroke yourself while you think of her, picture her standing over you. You're kneeling naked before her and she tells you that you're her sissy now. She's going to use you whenever she wants. If she wants to lock your cock away, she'll do that" the girl whispered in Jack's ear, guiding him through her little mental scene.

Jack did not want to be kneeling in his daydream, he wanted to be with Chrissy on her level. But as Jayne commanded it, he couldn't help but picture it. His hand stroked back and forth, beginning to pick up pace. He leaned back a bit, feeling the busty girl's chest holding him in place. It was a nice place to be resting, especially after such a long day. At the mention of chastity, Chris flinched. He had heard of chastity cages before but never saw one. Locking his dick away, but then he wouldn't be able to cum? The thought made him stroke a little bit faster, worried that one day someone may take away his ability to.

Jayne's breath was hot in Jack's ear, and she leaned forward to stick her tongue out, stuffing it inside of his canal. Her tongue swirled around inside of his head, causing Jack to have to stop what he was doing and quiver. She pulled her tongue out, smirking at how it had completely stopped Jack in his tracks. "Don't stop jerking sissy, you want to cum, don't you?" She continued her little scene, narrating for Jack. "Now, picture Chrissy leading you to bed. But instead of laying you on your back, she lays you on your stomach."

Jack continued to stroke, following along with Jayne's scene. His toes curled several times as he stopped himself from cumming, not wanting to blow his load too early and get in trouble. He pictured everything that Jayne was describing, Chrissy taking his hand and helping him into bed. Rolling him onto his stomach, his ass exposed for her to do whatever she wanted with it. He loved her, she could do what she wanted, he thought to himself as he daydreamed.

"She gets on top of you and you feel something on your back." Jayne pulled one of her hands away from his hips and brought it to his back, pressing a finger against the side of his butt. "Is that a strap on she's wearing? It feels big. You're nervous, but she runs her hands over your back. Raising the strap to your butt, she begins to press..." she trailed off, taking her finger and slipping it between Jack's buttcheeks. She only pressed against his hole lightly when it happened.

"FUCCKKK" Jack grunted out loudly as he felt the finger touch against his hole. He had been picturing it, dreaming it so lifelike that when Jayne touched him back there, she triggered his orgasm, sending him nearly falling forward. Jayne's hand on his waist was the only thing keeping him from faceplanting as his body had trouble finding its center while he came. He spurted across the room, getting his sheets even wetter than they were before. He crumpled to his knees, exhausted.

Letting Jack spasm by himself for a minute, Jayne's interest for the night had run its course. She gathered up her clothes from where she had tossed them and began to get dressed again. Settling her large chest back into her top, she picked up her leggings and put them on as well. "Well, I need a shower and you look like you need to be alone with your thoughts for a bit. Might want to do some laundry as well." Making sure she wasn't disheveled, Jayne walked over to Jack's door, turning back to him "And you know, I'm right next door. I can always help if you need it.

As Jayne left him on the floor alone, Jack's thoughts ran in all different directions and he was unable to pin any down. Too much had happened to be able to unpack it all today. He looked around his room and decided it would just be better to clean up and figure it all out tomorrow. He gathered up his bed sheets and threw them in his hamper, along with the clothes that Chrissy had left him. He had a feeling it would be better to keep them clean and headed off to the basement to wash today off his sheets.


	10. Chapter 10

Chapter 10

Waking up the next morning, Jack was glad it was the school week again; to have classes to take his mind from things. But as he went to get dressed the first pair of underwear on the top of his pile was Chrissy's thong. He looked at it and picked it up, wondering if he should wear it today. With no one around to encourage him on, he decided against it and stuffed it ashamedly to the back of his underwear drawer. He put on normal boys' underwear and normal boys' clothes before heading out to start his day. Jayne's door was closed, and Jack felt a pang of sadness, but decided it would be better for him to head off before she roped him into doing something else crazy.

He stopped by the school cafeteria and swiped his pass before getting breakfast. Loading his tray up with some cereal, an apple and a pop tart, Jack found a quiet table to sit at. He usually ate alone, or with Chrissy, but he did not really hang out with too many people on the regular. Looking around the cafeteria, he noticed the Alpha Chi dicks sitting together at a table. He grimaced, thinking about how if it were not for them, everything that had happened this weekend would not have happened. "You should thank them" came a disembodied voice. Jack looked around, but there was no one there.

"Up here dumbass, I'm in your head. You should thank them" the voice said again. It was his own thoughts! He smacked at his head lightly, hearing some light laughter as the voice faded away. Now he was hearing things. Jack finished his breakfast and left the cafeteria, making sure to avoid the Alphas. Jack walked across campus to his morning class.

The rest of his day was uneventful and as it dragged on, he found himself wishing that he were having more fun with Chrissy instead. He had texted her during lunch, but she had a busy week and was not going to be able to see him until the weekend. During his afternoon class he ended up falling asleep. Dreaming of Chrissy and Jayne together, both wielding large strap ons. He was kneeling before them and then...And then he woke up, drooling on his desk as other students filed out around him. Sitting up and wiping the saliva from his cheek, he went to stand up when he realized he had quite the raging hard on. He sat back down for several minutes and pretended to finish his notes as he waited for it to subside.

Closing the door to his bedroom behind himself, he made sure to lock it this time. Jack put down his bookbag and dove for his dresser. There on top was the outfit from yesterday. He took it out and set it on his desk, looking at it. It was not anything exceptionally sexy or revealing. There was not anything special about it. Why did it hold so much power over him?!

He was torn. Part of him wanted to throw it away, the other part wanted to put it on right then. He tapped his foot quickly; unaware he was even doing so as he tried to make a decision. "Oh, what the hell?" he said aloud, pulling his boy clothes from his body. In a few seconds they were in a pile and he was holding up the white thong, stretching it out in front of him. He went to step into it and stopped himself. There was a war raging inside of his body, pulling him in opposite directions. But the thong won out, and he stepped through it, pulling it up to his waist and settling into it. His face felt flush, but he continued.

Jack pulled the leggings on first, they were the easy part. The hard part was the bra. He did not HAVE to wear one, but he had been thinking of the way the fabric felt on his nipples all day. He had only realized it when he thought back on it, having too much going on in the moment when he first wore it. "Alright, maybe there's a guide online" he said, hopping on his computer. He googled how to put on a bra and found several informative videos. He opted for the cheating method and hooked it together before putting it on over his head.

He finished the outfit, pulling on the purple tank top but leaving out her hoodie. The top felt a bit more girly than the hoodie did. Sitting down in his computer chair, he pulled up his history and looked at the video that had started it all. His memory of it was a bit hazy, but he wanted to understand what had started it all.

An Asian "ladyboy" walked on screen, in a tiny black miniskirt that barely covered her ass. Underneath the skirt was an obvious bulge, but in his drunken state he had not noticed. He watched the video more intently than he usually did, checking out how she walked. He found himself calling the porn star a ‘her’, wondering what the difference was. "She looks like a her, you still look like a him" came the voice from the back of his head. He did not want to agree, but he had to say that if it wasn't for the bulge, he would have thought the star on the screen was a woman...Sober, he had to remind himself. He would think that even when he is sober.

Whether it was the video on his screen or the outfit he was wearing, his cock agreed. He could feel it getting hard, building on itself as the harder he got, the tighter the clothes were on him. It was not long until he had to pull it out and begin stroking or he thought he might cum in his leggings. He did not want to have to clean them again, but he did not want to take them off either.

"Just going to have to be careful" he said to himself, starting to stroke. With his free hand he took hold of his mouse and paused the current video. The star had begun to stroke herself as well, and it paused mid stroke. He stifled a laugh as her face was back in ecstasy, but he realized he probably looked even worse. He dragged the mouse over to related videos and began to look through it. He slowed down his stroking, not wanting to cum too quickly. He had some research to do.

Opening various videos, he started to play them to see what struck him. Solo videos of crossdressers and transgender girls playing with themselves, sometimes even using toys. "Lesbian" videos where a CD or TG had sex with a woman, sometimes being the bottom, sometimes the top. Finally, he opened a video of a man and a crossdresser having sex. His body had responded well to all of them, getting hard at the beginning and staying hard all the way through. Did that really mean...No, he was simply hard from the first videos and that was it. He closed the last one and began to watch the "Lesbian" one, stroking himself as he did.

When the crossdresser in the video started to bottom, he felt his orgasm beginning to well up. He grabbed some tissues from his desk and quickly brought them around the head of his dick, cumming into the wad as the CD moaned loudly with a strap on up his ass. Cleaning himself up and tossing the tissues, he quickly closed out of the videos like he usually did. He often lost sexual interest quite quickly after cumming, but now he had the quandary of the outfit he was wearing. Should he take it off or should he keep wearing it?

Not wanting to push his luck more than he already had, Jack pulled off the leggings and thong and kicked them away. He took the tank top off correctly this time, crossing his arms and peeling it off over his head and angled his arms to take off the bra. Gathering them all up while naked, he brought them to the dresser and went to drop them inside, but the thong fell outside of the dresser. He bent down to pick it up and admired it again.

"You know, they're not so bad..." he thought to himself, groaning as his will was weak and he found himself pulling the thong back on. Tucking his softening package into it, he pulled on the waistbands happily to tighten it around his cock. The fabric just felt so wonderful and he wondered how was ever going to go back to wearing boy underwear.

Grabbing a pair of shorts and a black hoodie, he covered himself up, the panties a secret underneath it all. He still needs to brush his teeth, so he gathered up his things and unlocked his door. Walking down the hallway, he realized he was smiling. He had a secret, and instead of feeling ashamed about it, it kind of made him happy. He was being more daring than he ever had been in high school. He was the guy who always chose Truth during Truth or Dare!

Walking into the bathroom, there was already two students at the three-sink fixture. Billy, the taller student from yesterday, was on the left and Jun, an Asian exchange student was on the right. He stepped up to the middle and nodded at the other two boys, slathering his toothbrush with toothpaste and beginning to brush his teeth. As he stood between the two guys, the white foam building up in his mouth, he thought of the videos. The toothbrush felt like a cock, rubbing over his lips and into his mouth.

Shaking his head as he tried to get the thought out, he could feel himself start to get hard again. "Already? And from thinking about that?!" he thought to himself, glad that he had worn a hoodie to the bathroom. He stepped closer to the counter, glad that he was wearing the thong and that his cock was pressed tight against his body. "Guess it's good for something" he thought, continuing to brush his teeth. He finished and headed back to his room, feeling proud of the first time he wore his underwear outside of his room.


	11. Chapter 11

Chapter 11

It was not until Thursday that he had any more fun, getting too caught up in his schoolwork. It almost felt like it may have been in his rearview until there was a knock at his door at night. Jayne stood there in the doorway, obviously having just came from the gym. She was wearing another matching workout outfit, this one with a purple and grey pattern. Stepping into Jack's room without asking, she held up a small gym bag and tossed it to him. "Don't say I never got you anything" She said with a laugh, allowing him to check it out as she walked over to his bed and hopped on it, even as sweaty as she was. "I raided the lost and found at the gym for anything I thought would fit you"

Jack opened the bag and was met with the smell of a gym locker room, gagging immediately. "Oh, that's ripe!" he said, waving his hand in front of him to get the smell away. But after the initial shock, he was hit with awe. The bag was full of clothes. Like, full full. There was training bras and workout bras. Leggings and bike shorts, even regular clothes like jeans and shirts.

"You'd be surprised how much stuff gets left behind there, it's a big school. Sure, you're going to have to wash it all, but sissies can't be choosers" she taunted, lounging out on his bed and covering the entire thing in her smell. "I figured you could try some on and then show me your thanks" She spread her legs wide, placing her hand on her crotch and mimicking rubbing. "Just go ahead and dump it out and pick something out that you think is hot. Don't worry about the smell, I'm probably worse" she laughed.

Jack grimaced, if she was worse than he was in for it but looking at the pile of clothes....it might be worth it. He sorted through them, separating bras and underwear, workout clothes and regular clothes. When he had a good idea of what was all there, he made some choices. He found a red and black pair of polka dot panties, along with a plain black training bra. He slipped those on to start, happy that it was so much easier to get into a trainer. Then he picked up a black pair of girls shorts that said "JUICY" across the butt and a crop top that showed off his plain stomach. Getting it all on.... he looked like a guy with terrible taste. He had no idea how to match clothes.

"Well, we'll have to teach you about taste, but at least you have things to wear now" Jayne laughed as she looked over his outfit choice. He had a long way to go, especially when it came to his face, but if she blocked that with her thumb his body looked feminine enough. "Might have to make you come with me to the gym for some booty sessions. We'll get you some curves in no time." She sat up and hooked her fingers into her bottoms, stripping them off and tossing them at Jack. They landed on his head and she laughed as he looked horrified. "Hey, are you saying that my pussy scares you that much sissy?" she taunted, getting onto her hands and knees. "Cause today, you're getting the other side."

He pulled the soaking workout shorts from his face, feeling like it left a sheen of her sweat all over him. But seeing her naked sex again made him instantly forget that she just uses him as a toy. "The...other side?" he asked, looking at her crotch and realizing she meant her ass. He gulped; her crotch had been strong the last time. He had never even eaten ass before, not even Chrissy's cute little one. But Jayne had gone above and beyond getting him these clothes, he couldn't say no. "How do you want me this time?"

Jayne smiled as her little toy gave in and submitted to her will. She pat the bed next to her and pulled off her top, releasing her chest. If there was anything holding Jack back, that just settled it. She made space for Jack as he nervously got onto the bed with her. She leaned over him, pressing her tits into his face. They were sweaty, but she pushed her breasts together and moved them towards his mouth. "Go ahead, give them a lick, but only one each. You've earned it."

Jack started to stick his tongue out, only to find to he was only allowed one lick each. Leaning forward, he pressed his lips to her left nipple and sucked it into his mouth, slathering it with his tongue. He looked up to see if that was alright, pulling back before he got in trouble and moving over to the other. Her nipples were a bit tangy, but he was still happy to tongue them. Having gotten his licks in, he lay back. "What now.... miss?" he asked, pulling a line from one of the movies he had watched.

Jayne was all too proud to hear the word "Miss" come out of Jack's mouth. "That's right, I am your mistress, aren't I? In every sense of the word." She pulled her chest away from his face and maneuvered her body around until she was squatting over Jack's face again, this time facing the other way. "And remember, it's my ass you're cleaning this time. I better not feel your tongue on my pussy unless I tell you." She lowered herself until she could feel her ass rubbing on his nose. "Go ahead and use your hands to spread me open, And I better not feel them move at all."

Knowing a command when he heard one, he replied with "Yes...Mistress" and raised his hands, carefully placing them on her cheeks. The familiar smell from the other day returned, getting stronger as she got closer. With his nose practically up her ass, he had no choice but to get a good whiff. He could tell that Jayne had put in a hard workout today. He powered through it and brought his mouth to her butthole, sticking his tongue out and lapping at it like a cat.

She could feel his tongue prodding at her hole, poking around like he was lost. "It's not a cock sweety, you can't get me off by licking around it." Spreading her legs wider to give him better access, her body also lowered, putting more weight on his face. Her cheeks covered his nostrils, cutting off his oxygen. She could feel him panicking underneath her as he couldn't breathe, so she put her hand on his chest firmly. "Relax, sissy relax. I'm not going to hurt you. Take a deep breath when you can and just let me know when you run out of air." She raised off him, allowing him the ability to breathe.

He gulped down the air as soon as he was able to, having been caught off guard the first time. Getting his heart rate back down, he got his nerves back up, ready to go again. "Alright I'm sorry.... mistress. I'm ready to go now" He said from underneath her, taking a deep breath before feeling her lower back down on him. His oxygen cut off again, he started to work. He stuck his tongue out hard and probed around until he found her hole. The taste was strong, but there was no point in focusing on that. He pressed his tongue against her hole, trying to work it inside of her but finding resistance. Even her butt muscles were strong! Feeling his breath begin to fade, he kicked his feet around, hoping that would work as a signal.

She felt him trying to tongue her hole, her toned ass giving his weak tongue trouble as he tried to put it in. “You can do it sissy, just get your tongue in there and wriggle it around like a good bitch” she coaxed trying to help him carry out his task. Seeing his legs begin to kick around, she groaned and lifted herself up, feeling him inhale heavily from beneath him. It was obvious that being underneath her was too much for him. Kicking her leg over him, she nudged him in the ribs. “Get up, we’re changing positions”

Jack felt like he had failed, worried that Jayne was going to get mad at him. “I’m sorry, did I do bad? I can do better” he began to plead with her. Everything felt like it was life or death now, one small slip up could lead to his life being ruined. He moved out of her way as she got herself comfortable, laying on her back again.

Jayne lay back for a moment as she gathered herself up, reaching out for her feet before pulling one behind her head. Even though she had some muscle, she knew how important flexibility was and stretched quite often. It too her a bit of work to get both feet behind her head, but now she had a better position for Jack, one she would be able to watch him from. “Alright, now you can get working. And if you can’t get your tongue in there just yet, use your fingers too.” She commanded.

He watched Jayne fold herself in half, quite impressed she was able to bend like that. Now that he was not going to be crushed underneath her, he felt a little less nervous. “Thanks Mistress...I’m sorry I couldn’t get it” he apologized, quickly getting into position in front of her. He lay down on his stomach facing her crotch, having to pull his legs up behind him to be able to fit onto the small bed with her. He kicked his legs around idly behind him as he leaned in to get back to work, kissing at her hole before trying to put his tongue in again. He took her advice to use his finger, looking up at her as he sucked on his index finger before working it inside of her.

Jayne watched him from between her legs, holding her legs back with her elbows. It certainly was not the most comfortable position for her, but she wanted her ass licked without having to worry about killing someone. As Jack’s finger slipped inside her, she rested her head back against her feet and moaned. His fingers were smaller than hers and she was certainly interested in seeing how well he could use them. “Sissy, if you’re not going to tongue my ass then you better tongue my cunt” she commanded.

Ever eager to answer to Jayne’s commands, he moved his mouth to her other hole as he fingered her ass. He was much more adept from this position where he was able to breathe and move his neck. He slipped his pointer finger in and out of her ass easily, pumping it as he ate her out. A strong hand on the back of his head pulled him deeper into her crotch, ceding the freedom he thought he would have. But the hand on the back of his head also spurred him on more. He had not known before, but he found himself answering increasingly well to authority. He had always made decisions for himself, and a lot of them seemed to be the wrong ones. Maybe he should listen to others.

Whatever epiphany Jack was having, Jayne was more focused on her pleasure. The boy's eager finger had slipped in so easily, but he did not seem to realize that she could take, that she needed, more than one. “Push in another finger sissy, fuck, come on work it!” she lorded, able to roughly move him even from her compromised position. “You want a soaking again don’t ya? You gotta work for your meal” she taunted, tugging on his hair as she tried to pull him inside her.

Remembering that he was here for her, and not himself, Jack picked up the pace and worked a second finger inside of her ass. He could feel her hole bearing down on his fingers, crushing them together. How could she be this strong even with her ass muscles? On the other end, his mouth latched onto Jayne’s clit and began to suck. It was the one thing he was good at as Jayne moaned in pleasure. Feeling a bit daring, he tried to push a third finger into her ass.

Feeling that third finger slip inside of her sent Jayne over the edge. She pulled his face back from her pussy with one hand, rubbing at her clit with the other. She clenched her jaw as she felt it coming, sending a wave of her juices cascading over his face. This time she got to watch as she soaked him, her juices dripping off his face and wetting the bed. It took her a few moments to finally unhook her legs from behind her head, rolling out exhausted.

Jack just managed to close his eyes as he was assaulted with her liquids, knowing that she was basically peeing on him. It was a dominance thing, he guessed, she was marking him. In an odd way, it was sweet. Letting as much of her juice drip off his face before reaching up to wipe enough away to open his eyes, he was disappointed to see she was putting her clothes back on. Last time, she had helped him...

“Aw what’s wrong sissy, did you want a handy even though I brought you all of those clothes? Well it was pretty good; you just make sure you keep deserving these alright?” She walked over to the bed where Jack was now kneeling, wrapping her hand around his body and spinning him around. “Mmm go ahead and take it out, you know I’m not going to do any work.”

Jack giggled as she easily moved his body like it was nothing, feeling nice and safe in her hands. He reached underneath the bottom of the shorts and pulled his cock out from below, leaving the gym shorts on. This way, his balls were still nestled by the soft underwear. Feeling clever with himself, he leaned back into Jayne’s arms, feeling one wrap around him. He felt the other hand groping at his ass, and he began to stroke himself.

“That’s a good sissy, you know exactly what you want right now, don’t you?” She spanked his ass firmly before raising her hand to his mouth. She pushed her middle finger in, probing the soft lining of his cheek. Getting her finger nice and wet, she pulled it back out and brought it down to his ass. “Stroke it really good for me Sissy. Chrissy should get first whack at fucking you, but that doesn’t mean we can’t have some fun.” Jayne’s wet finger disappeared under Jack’s short shorts, quickly working its way to his hole. He was tight, but she was strong, and her finger slid inside of him, locking him in place.

He had never had anything inside his ass before, and his first instinct was to yelp. The strong girl’s arm was still holding him in place, so there was nowhere he could move. But after the initial pain and shock subsided, he realized it was not that bad. His cock was harder than it had ever been before as he felt the foreign invader inside of him, and he kept stroking it vigorously. Pleasure was the only goal right now. “Thank you, Mistress,” he managed out, his face turning red.

But Jayne had a different idea. After allowing Jack to get himself hard, Jayne slipped her finger out. The boy whined, feeling suddenly empty. There was something missing, and he wanted it back. “I should have known you were a butt slut, don’t worry, Mistress will help.” Pushing Jack onto his back, she pushed his legs up to his chest, knowing he was not flexible enough to put them behind his head like her. With Jack balled up and his cock dangling over his face, she pulled away his shorts and spit on his asshole. “No using your hand sissy, just lay there” she commanded, forcing her fingers inside of him.

Completely at Jayne’s mercy, Jack had never felt so helpless but happy at the same time. He watched as his cock jumped in the air at the inclusion of her second finger, his body shivering as he got used to this new sensation. Jayne had mentioned Chrissy being the first to fuck him and now he began to picture it. Laying side by side in cute outfits as she played with his ass with a strap on, not having to do any work but just enjoying it. That would be the life.

Watched as Jack closed his eyes and cooed, happily taking her fingers as she shoved and twisted them around inside of him. “Open your eyes sissy, you’re going to want to see this” she said, waiting for him to obey before targeting his prostate. It did not take much of an assault before Jack’s cock jumped and pumped, shooting a load directly into his own face.

Jack had never known that the prostate was like that, he had thought that people just really liked the feeling (And after being fingered, he could see why!) of something in their ass. But when Jayne punished his prostate, the involuntary orgasm that he ended up spilling left him dazed. This was the first time he had come that was not even partially from his own doing. This was the first time he had truly cum as a submissive.

With Jack’s seed spilling out all over his face, Jayne’s work was done for the day. She got what she needed, and she had given as much as she got. Pulling her fingers out of him, she laughed as the boy continued to shudder. “Intense, isn’t it? I’m betting soon that will be the only way you cum” she teased, “I bet Chrissy will be glad to be on the other side of that power spectrum.”

Jack lay on his bed, wondering what to do about his load on his face. “You don’t think Chrissy will let me fuck her anymore?” he asked sadly. His sheets were already soaked with Jayne’s juices, so he leaned in and began to clean his cum off his face with his blankets. He had to do laundry anyway, but he definitely needed a shower as well.

“Why would she? She’s gotta be glad she doesn’t have to take that small thing if she doesn’t want.” Jayne was in a feisty mood after that last session, cumming hard always brought out the alpha in her. Seeing that her words were cutting, she gave her sissy a reassuring hug. “Don’t be sad about it, just think about how hard you came from two fingers and imagine what it will be like when the woman you love is on top of you with a toy. Anyway, I’ve got classwork to get done and you’ve got cleaning to do. Now you’ve gotta ask yourself, are you gonna wear your new clothes around Chrissy and let her know that someone else is helping you as well, or will you hide them?” And with that cryptic question, Jayne left Jack to wonder and worry.


	12. Chapter 12

Chapter 12

Worry, Jack did. He had until the weekend to come up with what to say to Chrissy, but each time he didn’t know what she would think. “Hey Chrissy, remember when you and my next-door neighbor walked in on me with my dick in a sock and Trans porn on the computer? Well she thought it was hot as well and has been getting me clothes to help me out.” He tried to think of a way he could lie that would work, but nothing he thought of sounded good.

“Oh, these clothes? I found them. Outside of my dorm room door. Yep, they just all happen to be my size and fell into my lap. DAMMIT!” he cursed, knowing that anything he told Chrissy about Jayne would likely lead to the end of their relationship, but he also couldn’t tell Jayne to stop doing what she was doing. He was between a rock and a hard place.

Friday was uneventful, but Saturday was going to be a big day. Chrissy had told him she wanted to spend the entire day with him, and she would pick him up from his dorm in the morning. Jack got up early and took a long shower, mulling over his quandary. He was going to have to be as truthful as he could be or run the risk of losing both of them. With that decided, he tackled his second biggest problem, what to wear.

Should he wear girl’s underwear? Or one of the outfits Jayne had gotten him? Or the one Chrissy had left him? Would Chrissy be weirded out if he was too eager? Or would she punish him if he was not eager enough? Once again, he decided to take the path of least resistance. He wore Chrissy’s underwear, with his own khaki cargo shorts and a green tee shirt on top of it. He could always say that he could not leave his dorm room in girl’s clothes, and that was true.

As a backup, he gathered up Chrissy’s first outfit, along with some of the new clothes, and stuffed them in the now clean gym bag. This way, he would have something to change into, and new clothes to show her, along with telling her the ‘truth’ about Jayne. All of his bases were covered and if everything went to plan, he would come out alright. It was ten AM and Chrissy should be there any moment.

The seconds ticked on for what seemed like hours, until his phone vibrated loudly on his desk. Hopping up, he grabbed the phone and checked the message, excited to see Chrissy’s name pop up. He grabbed the gym bag of clothes, along with his wallet and keys, and rushed out of his room to go meet her.

Leaning against her early 00’s red Mustang, Chrissy waited for her boyfriend for the special day she had planned. It had been a trying week with exams and interviews, and she had missed her boyfriend. Over the week she had found herself thinking differently of him, of all of the fun and naughty things they could do with Jack looking like a girl instead of a boy. The places they could go. When she saw Jack appear at the door everything from the week melted away and she rushed forward to meet him. She wrapped her arms around him, putting her head against his shoulder.

Jack was just as excited to see her, meeting her back with a full body hug. They rocked back and forth in the middle of the walkway, neither wanting to break away from the others embrace. “I missed you too” Jack laughed, feeling her hug him like they hadn’t seen each other in years instead of just a week. He angled his head to give her a kiss, pressing his lips to hers for several seconds. “I’ve been thinking of last weekend all week.”

Chrissy smiled at the sound of that. She had hoped last weekend wasn’t too much and Jack still wanted this. Looking around to see that no one was around, her finger slipped under his shirt and rubbed against his bare skin. Diving underneath the waistline of his shorts, she felt the band of the panties she had given him last week, which caused her face to light up. “Good, I’m glad you wore them! I have a lot of fun planned for today, but that’s later. Let’s get brunch first?”

After a quick brunch at the local café, Jack grimaced as Chrissy reached for the check, pulling it away from him. “Hey, I can get that, you don’t always have to use your parent’s money to pay for things, you know” he said, sinking back into his chair. He felt grumpy over it, relieved that he didn’t have to break open his skimpy wallet but saddened that he couldn’t provide for her.

“Relax babe” she said, placing her hand on his while looking around to see that no one was in earshot “I just wanted to treat my girlfriend to a nice meal” she said with a wink. She fished her dad’s card out of her purse and placed it in the booklet before the waitress came back to take it. “You don’t have to worry about things, you know I love you for a lot of other reasons than paying for dinner.”

Jack’s cock had an odd reaction to being called Chrissy’s ‘girlfriend’. Something about it seemed so demeaning, like his position had been lowered. But at the same time, he could feel the blood rushing into his panties. It was hot that she had said that, and he could feel his ears turn a little red as he blushed. “Well then, girlfriend, what else did you have planned for us today?” He asked, leaning forward to put his elbows on the table before resting his face on his hands, looking at Chrissy dreamily.

She leaned in “You really wanna know? You really, really wanna know?” each word brought her closer to Jack’s face until she kissed him on the lips. “You’re just going to have to follow me and find out” she answered coyly, sitting back until the waitress returned with her credit card. Getting up from the table, she reached her hand back to lead Jack to the next adventure. “Are you ready?”


	13. Chapter 13

Chapter 13

Leading Jack into the strip mall that was attached to the restaurant they had dined at, Chrissy held his hand tightly, swinging their arms between them slightly. She walked over to a store with interesting graffiti all over the front windows. To someone who had never been in there, it might look like the store had been tagged by vandals, but it was actually part of their look. Opening the door, Chrissy led Jack into Provocative Couture.

Jack stood like a deer in headlights as they walked into the store. His head swam as every which way he looked was the skimpiest and most interesting women’s underwear and lingerie he had ever seen. He was excited, but a little fearful. Were they here for something for him? Or something for her? He wasn’t sure if he was ready for a clerk to know his secret. He looked towards Chrissy, hoping she would let on to why they were there, but she was too busy looking around.

“Oh boy these are so cute!” she exclaimed, picking up a pair of pink panties with a lacy pattern. When she turned them around, she revealed that the back was non-existent, two strips of fabric connected the front to the back by looping under the crotch. She flipped the underwear over her arm, using it as a tray for her to put the clothes she liked on. Searching around the store for the cutest things, she built up quite the pile on her arms.

Jack was confused, after the ass-less panties he assumed that they were shopping for him, but as Chrissy began to pick out other things, he was unsure. He stuffed his hands in his pockets as he followed along, not knowing whether he should try to pick out anything himself and looked like the quintessential tagalong boyfriend.

Chrissy took the pile of clothes and walked up to the female clerk, asking to be able to use a changing room. The clerk unlocked one of the rooms and Chrissy stepped inside, closing it to leave Jack on the outside. She could see the pain in his eyes as it closed, wondering whether it was because he couldn’t watch her change, or because he wanted to change himself. Stripping out of her outfit, she put on one of the pairs of black panties and a black corset, lacing it up loosely as she could. “Hey babe, wanna see? Is the clerk looking?” she asked, whispering through the door to Jack.

Jack looked over to see that the clerk was doing paperwork, seemingly engrossed in it. He moved closer to the door, whispering back “She’s not looking back babe, why?” His question was answered by the door opening and a hand grabbing his shirt, pulling him inside. He stumbled but was careful not to fall over loudly, staring at Chrissy in the lingerie she had chosen. Words escaped him as he had never seen her dressed up like this.

“What’dya think?” she asked, putting her hands on her hips and cocking her body slightly to the side. Chrissy felt powerful wearing a corset, her fingers rubbing on the fabric near her waist. She was definitely going to get this one, but they were here for something else as well. Reaching out for Jack’s shorts, she gave them a tug “But you can look at me in this all you want later, quick take your pants off.”

That is what Jack had been nervous about. At any second the clerk could see that he wasn’t standing outside of the room anymore and come bust them. But he had trouble saying no to Chrissy, and the naughtiness of it all was quite fun. He made up his mind quickly began to strip, gripping his panties as well. “The thong too?” he whispered, playfully pulling the waistband up and down as he waited for an answer.

Chrissy giggled as she watched her boyfriend pull off his khaki shorts, exposing his girly underwear. She wondered how long it would take for her to get used to that, but she hoped never because every time was more special than the last. Picking up the assless panties that she had first shown, she handed them to him. “Alright now put these on, and quickly, the clerk could be back any moment.”

Jack pulled off his thong, leaving it on top of his shorts and took the panties she handed them to him. Pulling them up to his waist, he felt the familiar sensation as the fabric cupped his balls and package, but the feeling of having a string up his ass wasn’t there. He couldn’t decide if he liked it more that way or not. He turned towards the mirror to get a better look.

“Not here dummy, we could get caught! You’ll have plenty of time to look at them at home. Now put your shorts back on!” Chrissy grabbed the cargo shorts from the floor and shoved them into his hands.

Jack groaned, wanting to see what the back of it looked like but instead he listened to Chrissy. Taking his khakis from her hands, he quickly slipped into them, feeling the material more roughly on the bare skin of his ass than before. This is why women’s clothes are so much softer than men’s, he thought to himself, quickly zipping and buttoning his shorts. “Now what?” he asked before being shoved out of the door.

Chrissy giggled, now alone to try on the rest of the clothes she had chosen. “Now, just don’t get caught smuggling those” she whispered back. She ran through the rest of the outfits, taking her time to let Jack stew outside in his new undies. Finally make her decisions, she put back on her own outfit and gathered up the things she had chosen.

Jack smiled like a lost puppy finding its owner when Chrissy opened the changing room door again, his joy quickly turning down a little as he saw his girlfriend in the clothes she had worn into the store. He had been hoping to see more options, but he was just going to have to settle for what he already saw. He followed Chrissy up to the counter, standing back as she did her business.

“I’ll take these, and the rest can go back” she said, splitting the clothes about half and half. The clerk began to ring everything up, taking the tags off and placing it all in a nice little box before putting it in a big pink and black bag. “That will be $384.26” The clerk informed Chrissy, a number that hit most people her age like a hammer. She pulled out Daddy’s credit card and handed it to the clerk, not thinking anything of it.

Jack was jealous, but he couldn’t figure out why. Was he jealous that she was able to buy any of the clothes that she wanted thanks to her parent’s money? Or was he jealous that she was able to buy all of these sexy women’s clothes while he was left to the lost and found hand me downs?

Chrissy took the bag from the clerk and handed it to Jack to hold. She was so happy now that she was getting the best of both worlds out of her relationship. “Thanks for your help, these clothes are so great!” she told the clerk before turning with Jack to leave. But as they approached the door, the security alarm went off.

Jack froze up. He hadn’t thought of it when he saw the clerk taking off the security tags at the counter, there must be a tag somewhere on the panties he had taken! Was he found out? Was he going to have to strip and show this clerk that he had girl’s underwear on? Was he going to get arrested for it?”


	14. Chapter 14

Chapter 14

“Just go ahead, that’s been doing that all day” said the clerk, waving them out the door.

Jack’s legs didn’t want to work at first, and he stood there stuck in place. He had been so scared that something had snapped, but the feeling of Chrissy’s hand on his brought him back. He stumbled out of the door with her, breathing harder than he ever had in his life. Once they were far enough away from the store he turned to Chrissy “I cannot believe that happened, I was so scared I thought I was going to wet myself” he admitted, holding his hand to his chest to calm down his breathing.

“Aw baby was that your first-time stealing clothes?” she asked, not as concerned by it as Jack was. Even though she had the means to buy everything, she couldn’t help but have sticky fingers sometimes. Turning to see that it had really affected Jack, she took the bag from his hand and put it on the floor. Reaching up, she cupped his face with her hands “Don’t worry sweety, I won’t let anything bad happen to you. I would have told her it was me.”

Feeling her hands on his face comforted him. He didn’t know why this was setting him off so much, but she was there for him. He lunged forward to wrap her up in his arms, sniffling gently. “Thank you, babe. This has all been kind of scary, but I’m just glad that you’re at my side to lead me through it” he admitted, every word of it was true. He had never planned or expected this, but it had brought him closer to his girlfriend.

Chrissy snuggled right back into him, loving the affection. They didn’t really have many problems in their relationship, but they had never hugged like they were right now. Finally breaking away, Chrissy scanned Jake’s face to make sure he was alright. “I promise, nothing bad, alright? Now, we have a lot more fun ahead of us...unless you wanna stay here until that clerk realizes there really is something missing” she giggled, the two of them heading back to her car.

Jack hopped out of the car as they arrived at Chrissy’s apartment, finally somewhere safe where it would just be them. He picked up Chrissy’s bag from the back to carry for her, as well as his gym bag of clothes. He followed her into the lobby, looking a bit like her valet as he carried so much. They rode the elevator up to her floor, the camera peering down on them reminding them not to get handsy.

Chrissy unlocked the door to her apartment and began to put her things down on the counter/ She really enjoyed having her own place and not having to deal with all of the Dorm Drama. She also didn’t have any trouble with making friends, so it wasn’t like she needed to be in the thick of things to find the action. And it gave her all the privacy in the world without nosey neighbors bothering them. Finally, alone together, she grabbed Jack and pulled at his shirt. “Take it all off right here” she said sweetly.

Jack’s eyes lit up. They were finally somewhere safe, and he had been dreaming about this all week. He eagerly pulled his shirt off over his head, not even thinking as he crossed his arms the way Jayne had taught him. Unbuttoning his shorts, he left his boy clothes in a pile at her front door. He went to hook his fingers into his new panties, but Chrissy stopped him.

“Wait, those can stay on” she said, biting her lip as he looked so cute in them. With her still fully clothed and Jack only in panties, she stepped to him and began to circle. “This is what you want, isn’t it? You love to be girly with me, like it’s our cute lesbian secret, right?” Her finger traced a line over his lower back. “I’m perfectly fine with it, in fact, I absolutely love it. I just want to make sure that you know what you’re doing.”

Jack stood still, feeling like he was being inspected. He shivered as Chrissy touched him, her finger sending electricity through his body. This was his chance to back out, to say that it was all a mistake that went too far. She sounded like she would understand. When she mentioned that it was like they were lesbians, his mind began to run. He thought about both of them wearing dresses to go out to eat somewhere, cute little nights dressed in soft PJs. He didn’t know why that sounded so much better to him than a normal relationship as a boy, but it got his cock going. “That’s exactly what I want babe, as long as it's with you.”

Getting confirmation that this was in fact what Jack wanted made her smile. “Good, we have so much to do today.” Turning away from him, she began to walk away, turning back to offer him her hand. “Don’t be scared, it’s going to be so much fun.” She led him into her bathroom and had him stand in front of the mirror. Kneeling down, Chrissy opened one of her cabinets and rifled through it. She pulled out all kinds of bottles until, finally, she found the correct one.

Jack felt nervous as he stood in her bathroom in just a tiny pair of panties...panties he had just recently stolen, mind you. He had never seen Chrissy so happy, and he was just glad to be the one to make her happy. But she hadn’t explained what they were doing today, and curiosity was beginning to get the better of him. “What are you looking for babe?” he finally asked.

Standing up with a large bottle that looked like lotion, she held it up. “Well, you know how much you loved that soft feeling when I shaved you? This stuff removes body hair much easier and leaves you a lot smoother for longer.” She pulled out a thing of latex gloves, pulling one out and slipping it on her hand. “I will warn you; it’s going to burn a little, but that just means it’s working.” She started to rub the lotion all over his back, the thick cream leaving a white layer on his skin. Chrissy stopped and groaned, “I don’t want to get your new panties all dirty, so now you’re going to have to take them off.”

Jack heard her say ‘burn’ and got a little fearful, but when her hand brought the lotion to his body he jerked forward for a different reason “AHH COLD!” he moaned out, his arms curling into his body defensively out of reflex. Getting over the initial shock, the cream began to warm up as Chrissy covered him with more. He agreed that he didn’t want to get his new panties dirty, not after all he went through to get them, so he slipped out of them and stood there naked.

Chrissy was sad to see the cute panties go and got back to working on covering him. She picked up a second glove so she could work faster, knowing that the longer the lotion was on, the more it would start to burn. She worked on the large swaths of skin firs, such as his back and his chest. Then she moved on to his legs and arms, getting it all of the way down to his fingers and toes. “I know you don’t have hair there but trust me, it’ll feel so soft when this is done. Now, spread your legs a bit.”

Jack could begin to feel what she meant by burn as the earlier swath of lotion began to get hot. “Oh, I can feel it...it does kinda burn!” he said nervously, his entire body was covered in this stuff! But he wanted to be perfect for Chrissy, so he bit his lip and bore it. When she asked him to spread his legs, he was a bit hesitant. “Isn’t it going to...hurt there?”

Chrissy nodded “Only a little, I use this stuff on my panty line though so if I can handle it so can you” she giggled, watching as Jack gently spread his legs a little bit more. She swiped the lotion between his legs, covering the underside of his balls, his taint and his butthole. Reaching again from behind, her hand grabbed for his cock, spreading it there as well. “Alright, now that’s everything. Go stand outside for 10 minutes and I’ll let you back in when I’m ready” she said, shooing the naked boy out of the door.


	15. Chapter 15

Chapter 15

As it locked behind him, Jack had no idea what to do now. He couldn’t sit, not wanting to get the cream all over her sheets or furniture. He couldn’t even stand in a comfortable manner as he had to keep his arms and legs spread to keep from sticking to himself. He could hear the bathtub start to run inside, wondering what she was doing in there. As time ticked on, the burning sensation began to get worse. He was even feeling it in his nether region, getting worried that Chrissy wouldn’t let him back in in time.

But then the door opened, revealing a dark room. There was a glow from inside, and Chrissy stepped into the door frame. Her body was naked except for a sheer bath robe that flowed around her. Chrissy raised a finger and curled it, calling Jack from across the room. She turned and walked into the bathroom, waiting for him to follow.

Jack was awestruck. He had seen Chrissy naked plenty of times before, but something about the way she carried herself this time was different. He followed into the bathroom; the lights turned off except for a smattering of candles flickering around the room. The bathtub was full of water and rose petals, light wisps of steam coming off the surface of the water. “You’re going to want to shower first, but then you should join me in the bath.” Chrissy turned away and the bathrobe slipped from her body, falling to the floor as she got into the hot tub, turning back to face Jack.

The young man wanted to dive face first into the shallow tub right there, every part of him ached for Chrissy. But all of his body burned as well, the hair removal ointment having done its job quite well. He looked back and forth from the bathtub to the shower and then quickly hopped into the glass enclosure. Turning on the water, he didn’t even care how cold it was, as long as it washed this stuff off him. Allowing his less sensitive areas to take the heat, he ran the water over his cock and ass first, not wanting to feel the burn there.

Chrissy looked on from the bath, giggling as her boyfriend dove for relief. She sat back in her tub, letting the hot water relax her. A rose petal stuck to her tummy and she blew it off, watching it go back to floating on the water. “I promise it won’t be so bad next time, plus this stuff lasts for like, at least a month” she added, waiting for Jack to be done. She wanted to feel his body on hers!

Scrubbing the remaining ointment from his body, Jack was surprised by how smooth his skin was. He had thought that the cream only removed his hair, he didn’t know it softened his skin as well. He ran his finger over his stomach, watching it glide. He ran it over his ass, the skin there even smoother than it was from Chrissy shaving it. Turning a bit, he saw Chrissy watching him enjoy his new skin. Jack turned off the water and stepped out of the shower, dripping all over as he moved to the bath. “Oh, fuck that’s hot!” he exclaimed as he got in, ruining their cute little moment.

Chrissy giggled, of course the water was hot, she loved it hot. “It’s not that bad silly, calm down. Now come here?” She spread her legs open to make space for him between them, and Jack acquiesced, leaning towards her as they were face to face. Chrissy stopped him and twisted him around, sitting him between her legs. Her chest pressed to his back, she wrapped her arms and legs around him, holding on to him tightly.

Jack hadn’t been thinking that was what she wanted. He was hoping to have a little...fun...after all that work. But when Chrissy flipped him over, he realized that just wasn’t in the cards right now. The feeling of her nipples on his back began to get him hard, surprising even him. “Your skin feels so good on mine” he moaned as he lay back against her.

“I know silly, that’s one of the best things about girl on girl” she teased. She brought her legs over his, sliding them back and forth over his thighs so he could really feel it. “Rub your legs together as well, trust me” she advised, wanting Jack to have the absolute best time. She brought her hands to his chest, lightly tracing lines over his skin with the side of her finger.

Jack didn’t even care as she referred to him as a girl, the sensation he was feeling now was more than worth it. He listened as she told him to rub his legs together, it wasn’t a command like Jayne gave him, but it made him want to do it that much more. Slowly moving his knees up and down, he rubbed his skinny legs together, compounded by Chrissy rubbing hers on his. She was right, this felt great!

Chrissy had never done this before, taking control like she was. Jack was putty in her hands, and it made her feel important. Running one of her hands up to his throat, she gently took hold of it. She had never been choked, or choked someone, so she didn’t want to tighten her grip. Instead, she spread her fingers out to creep up onto his cheek, twisting him around to kiss her. She rolled her hips forward, pressing her pelvis into his back for some stimulation, this was all getting her so hot!

Jack closed his eyes as he felt Chrissy’s dainty fingers wrapping around his throat. She had never been this kinky before, and his cock was raging above the water from all of the new feelings. She wasn’t larger than him like Jayne was, but he still felt so safe and comfortable in her arms. Returning her kiss, he twisted his body around a little so he could face her better, wanting to show her how much he was enjoying all of this.

Chrissy had planned things differently; she had wanted to doll Jack up completely before they did anything, but she was having trouble holding back. She would just have to rearrange things a little. Holding Jack’s chin to break off their kiss, she couldn’t help with how cute he looked. Giving him another small peck, she pushed his body forward so she could stand up. “I need to do something. Get dry in here and I will give you an outfit to put on, then meet me in my bedroom.” She dripped water all over the floor as she got up and grabbed for a towel, wrapping it around her body and walking out of the bathroom.

The sudden stoppage of play caught Jack off guard, wondering if he had done something wrong. He sat back in the bath for a minute, watching the steam still rise from the bath. He loved Chrissy but he didn’t know if he was ever going to take a bath with her again, it was blistering!

After another minute had passed, the bathroom door opened slightly and Chrissy’s hand came through, holding some clothes. He looked up from the tub, hoping to see her but she hid behind the door. “Here’s your outfit babe, take your time, it should take me a bit longer than you” she giggled happily and closed the door again.

Jack felt relieved as Chrissy dropped off the clothes for him, his mind at rest that he hadn’t scared her off. But now he was wondering what she was doing out there. He heard a hair dryer start up in the other room and figured it would take her some time, so he relaxed in the bath for a few more minutes. When he felt his fingers begin to get prune-y he figured that was enough waiting. Getting out of the bath, he found a towel and wrapped it around himself, shuddering as the soft material rubbed against his skin. Did everything feel this good to girls, he wondered to himself, how do they stop themselves from just rubbing up on anything?

Jack took his time drying off, enjoying the sensation of the towel everywhere. Remembering that he still had to get dressed, he walked over to see what Chrissy had given him. There was his panties from earlier, which he had been hoping for. After the scare he took to get them, damn right he was going to wear them. He pulled them up tightly, adjusting his package as best he could inside of it. He was still hard, and it just wouldn’t seem to go down! Picking up the rest of the clothes, he was surprised to see that they weren’t that slutty. He lifted one piece of fabric and it unrolled into a long skirt with a cute floral pattern. The waistband was elastic, so he opened it up and stepped inside. He wasn’t used to his clothes not having a crotch and swayed back and forth a little to watch the fabric move.

There was a pink bra to match the pink panties, and he again cheated by hooking it before pulling it on. He reminded himself to ask Chrissy later how to really put one on, he wanted to do everything right for her. He had never seen the top before, it was pink as well and said “Princess” across the chest in a font that reminded him of ‘Gisney’. The outfit was so comfy, especially with his skin so smooth now. He checked himself out in the mirror, a little disappointed to see that the femininity had not spread to his face. He still looked like a boy, just in girl’s clothes. “Well, aren’t you one, or is that not what you want to be anymore?” The voice from the back of his head asked.

A knock at the door shook Jack from his thoughts, reminding him that Chrissy was out there waiting. “Coming! I mean, coming out! I mean...goddamnit!” he cursed, unable to respond without a double entendre. Giving up, he walked to the door and opened it.


	16. Chapter 16

Chapter 16

Chrissy waited for the door to open, wondering what was taking her boyfriend so long with his outfit. She had dried off, blown and straightened her hair, threw on some quick make up and gotten dressed, all before he could just get dressed. She put her hands on her hips, the tight black corset she had checked out earlier correctly tightened to her body giving her the perfect hourglass. A shiny pair of purple latex panties clung tightly to her crotch, with fishnets and thigh high boots to complete the look. She was supposed to look like a dominatrix, but when Jack stepped out in his outfit, she immediately broke character. “Oh, my, god, you look fucking adorable” she exclaimed, stepping forward to check him out.

Jack was just as in awe of Chrissy’s outfit, for a second, he almost didn’t recognize her the way she had styled her hair and everything. “And you look so fucking hot” he responded, checking out the outfit she was wearing. Even when she dressed up for a night out, she had never looked like this before. “Looks like I should be calling you mistress” he teased, hoping he didn’t overplay his hand and let on that he had been looking at those kinds of things.

Remembering the character she had come up with and her entire plan, she stepped back, stiffening her lip. “As a matter of fact, you should” she said with a wink, not wanting to freak Jack out too much. She turned away from him and stood at the edge of her bed. Snapping her fingers, she pointed at the floor in front of her. “Come kneel before your mistress...Slave” she said, trying to give her voice some authority.

Chrissy sounded too sweet to really be a dominatrix, but Jack was absolutely loving it. He flit towards Chrissy, his skirt flowing around in the air as he moved. The feeling of the fabric rubbing against his smooth skin kept him hard, and each step the panties rubbed on him. By the time he knelt in front of Chrissy, he felt like he was ready to bust. Looking up at her, he would do anything for the woman who stood over him. “What would you like now, Mistress?” he asked, trying to raise his voice to sound like a girl.

Bending down to meet his gaze, Chrissy’s chest barely stayed in the corset. She lifted a finger to Jack’s chin, holding him in place. “That’s my good little slave, you love your Mistress, don’t you? You would do anything to make her feel good. Even dressing up in girl’s clothes, there’s nothing you wouldn’t do, is there?”

Jack nodded his head. The way Chrissy paused to say “Slave” was just too cute, she was trying so hard! But he loved that she was doing it, it made him feel so special. “I would do anything for you Mistress, isn’t my outfit so cute?” he asked, puffing his chest out to show that it said Princess.

“It is just adorable, and it all fits you so well, just like it was made for you. Boys are always so scared to wear girl’s clothes, but not you, you’re eager to.” She slowly sat on the edge of the bed, spreading her legs wide. “Eager to do anything to please your Mistress, like kissing me here?” Chrissy pointed at the top of her shiny black footwear, not realizing she was asking instead of telling.

“Of course, Mistress, anything” Jack replied. He put his hands to the ground to support himself, lowering his face to the top of Chrissy’s high heels and kissed it sweetly.

“And what about.... here?” Chrissy asked, pointing higher up on her shin. She smiled as Jack raised himself up a little, kissing the spot she pointed at. She continued up her leg, having him kiss her knee, her thigh, right below her pussy and then the crotch of her latex panties. His first task complete, Chrissy leaned in towards his face again. “And is all of this getting you...excited?” she asked with a twinkle in her eyes.

Jack nodded his head happily, his face turning a little red. “Yes Mistress, so very excited. Would you like to see?” The skirt was trapped under his knees, so he pushed off of the ground a little to pull it free. Remaining kneeling, he pulled the hem of the skirt slowly up his thighs. He bit his lip as it softly ran over his skin. Soon the skirt was pulled up to his crotch, and he lifted it up to show that his hard cock was just spilling over the top of his panties.

Chrissy clasped her hand to her mouth as Jack revealed his cock. It was the perfect combination of girly and manly, hard as a rock yet spilling out of cute pink panties. She was having trouble continuing because she wanted him so badly. “Oh my, it looks like someone is aching for their Mistress! I think you’ve been a good slave, so you deserve a little treat” She reached her hands out to help him up from his knees.

Jack beamed as Chrissy looked happy. He never would have guessed that putting on panties would make her like this, but he was loving it. He took her hands and accepted her help up, finding himself being pulled onto the bed in place of Chrissy. His “mistress” was getting to her knees in front of him! He looked down in time to see her lift the hem of the skirt and disappear beneath it, placing his hands back on the bed as he felt he was going to need to support himself.

Using the skirt as her little tent, Chrissy ran her hands up Jack’s thighs and felt him shudder, nearly falling back against the bed. This was another one of those fun things that could only be done with a crossdresser! Leaning in, she kissed the crotch of his panties, feeling his stiff cock through the fabric. She gently reached up to pull the boys panties down, hearing him moan as the panties moved. She slipped the panties down over his balls, letting his shaft pop forward. Slowly, she wrapped her fingers around it one at a time. With her hand covering most of the shaft, she leaned forward and began to suck on the head. She made no attempt to move her hand, mercilessly teasing the young boys’ cock as she swirled her tongue around on his helmet.

Jack couldn’t see what was happening, but he could feel it all ten times over. He had never felt this sensitive before, it was like every sensation was turned up to 11. His toes began to curl as he felt her bobble around on the head of his cock. He wanted her to move, to jerk, to suck him down, but she was teasing him so much. He was already breathing hard, making sweet little moans with each one of Chrissy’s movements.

Chrissy let go of Jack’s cock, hearing a whimper from outside of her little tent. She pulled the skirt off over her head, her face a little red herself. “Get a condom on babe” she said with some urgency. She sat on the edge of the bed and quickly unzipped her heels, tossing them off.


	17. Chapter 17

Chapter 17

Jack wondered why she had stopped, until she told him to get a condom. H wasn’t ever going to say no to that. As she began to strip, he went to her nightstand where she kept them. He grabbed one of the packages and began to try to tear at it, having troubles with it. He twisted it in his fingers, he tried to bite it, no matter what he did it wouldn’t open.

Chrissy had peeled her latex panties off, the inside of the underwear wet with her juices as the latex didn’t allow it to soak through. Seeing that Jack was still fumbling with the condom, she giggled. “Here, give it to me and sit near my pillows” she told him, taking the foil package and biting into it roughly. The package broke in her mouth and the condom fell out into her hand. “Success!” she said, holding it up like it was the secret of life.

Jack obeyed and moved up to the head of her bed as Chrissy tore the package open. He took some pillows and put them behind his back, fluffing them up so he would have a nice little nest. As Chrissy broke the package open, he was relieved. For a moment he thought they wouldn’t be able to get it open and would just have to stop. He held his hand out for her to give it to him.

Chrissy swatted his hand away, taking Jack’s skirt and running it up his body. She took the condom and slid it on over his cock, stroking it a few times to make sure it was nicely in place. He was still as hard as he was earlier and she felt proud, knowing that a big part of that was her. Pulling herself to a position straddling his body, she reached between them and guided his cock to her waiting pussy. Slowly, she lowered herself down and felt him slide inside of her.

The eager boy gasped slightly as his cock disappeared into his girlfriend. He had been worried that with everything going on, they wouldn’t be having sex like this anymore. But as Chrissy plunged on him, all those worries disappeared. Usually she needed a little tongue encouragement to get her going but today he could feel how wet she was on his thighs! Jack reached around her to hold her ass, wanting to contribute somehow as Chrissy maneuvered herself. However, that was short lived.

Chrissy removed his hands and pushed them back against her headrest. “No getting handsy slave, not unless your Mistress commands it” she moaned, holding on to his wrists as she fucked herself. Jack wasn’t huge, but Chrissy didn’t mind, he was just the right size to fill her up and not hurt. Leaning over to her nightstand, he slipped out of her as she opened her drawer. Pulling out two pairs of handcuffs, she opened one and clicked it against the post of her headrest. Holding out her hand, she commanded Jack “Give me your hand.”

His cock stood at attention, aching to be replaced back inside of Chrissy’s love canyon. He had never been cuffed before, not by the police, nor in bed. He nervously extended his arm, feeling metal clasp around his arm. He pulled against it, not to get out but just to see that it was real and felt pain in his wrist as he tightened the metal. They were definitely real.

Chrissy leaned over to the other bed post and latched the second pair of cuffs on, picking up Jack’s other arm to restrain. With total control of him, she straddled his dick again. But instead of lowering down all of the way, she rested her pussy gentle on top of him. She brought her lips just shy of his, her breathe hot on his lips. “Tell me you love me” she whispered.

Matching her tone, he whispered back “I love you Mistress”. He was rewarded with the feeling of her tightness wrapped around his dick, the entirety of his length slipping inside of her. “Oh, fuck me!” he yelled out, feeling Chrissy ride him with more gusto than she ever had. He was having trouble keeping quiet and soon felt a hand on his throat again, then the other. They began to tighten lightly, enough to feel like he needed to work for his breath.

Chrissy bounced her body up and down, driven like never before. This was real love, this was what she was looking for, this was getting her wet like nothing she had ever felt. She found her hands at his throat, squeezing. She leaned in and pressed her lips to his, controlling his breath. She had never had power in a relationship before, and it was a heady brew.

Returning her kiss, Jack’s head was swimming. He was trying to focus on kissing her, but everything was feeling fuzzy. She had sped up, but he was beginning to slowly go to sleep. His head lulled, his lips no longer moving and felt darkness closing in around him...and then everything came rushing back as her hands pulled away from his throat, the oxygen flooding his lungs. She was screaming and bouncing in his lap and before he could even get his bearings, he was cumming. His body tensed up as he felt like a rocket had just taken off from his lap.

Chrissy had cum hard when Jack began to pass out, the lengthy aftershocks lasting well after he had woken up. She leaned her head in against his chest, gripping the Princess shirt tightly. She couldn’t speak, only breathe, as she tried to get feeling back in her toes. That had never happened to her before and it took a minute to draw herself back up. The reservoir tip of the condom slipped out of her, revealing an ample load, but she made no move to take it off of him.

Chrissy went back to her nightstand drawer, opening it up and looking inside. Looking back at Jack as he lay in the afterglow, she knew she wanted to help him with everything. She reached inside the drawer and pulled out the slim white toy. It was small plain vibrator, just a cheap one that she could get without daddy recognizing it on her card. She picked up the skinny toy and smacked it against her other hand. “Now it's time for me to do you.”

End of Part 1


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